This year, I have completely revamped my tax tip structure. It’s time to think of tax concepts in big broad general categories, and then analyze the details later. Accordingly, I have realized that with the numerous tax law changes that seem to be coming faster and faster, and with the ever increasing expansion of the details and nuances of each tax idea, that there is too much information that can make the concepts get lost. Therefore, I have structured these tips in a format that is meant to be used as check list. They are grouped into broad categories. For example, there are tips related to being a homeowner, tips related to investments, tips related to owning your own business, etc. After all, it’s easy to go back and look up the details later if you think one of these may apply to you. I certainly can’t remember the details anyway. It’s the concepts that are important. These tips each have a vast amount of detail behind them such as AGI limitations, and other numerous considerations. However, just seeing the tip below will allow you to look up these details later and see if the tip can save you money. In fact, I recommend actually running the numbers with tax software to determine the actual impact of savings these tips will give you.
I have tried to structure the tips below in a bullet point manner, and also include where on your tax return these may apply (i.e. itemized deductions, schedule C, etc). I believe this will greatly improve your chances of actually using this check list and hopefully even if only 1 or 2 apply, you will save some nice money on your taxes. I also want to make sure you’re aware of one very important “tip” if you will. I just learned in a class I took called “Super Advanced IRS Problem Resolutions” that the IRS is ramping up big time. The current administration has and apparently is going to continue allocating huge dollars to the IRS’s enforcement budget. This means thousands of new IRS collection agents, more audits, and more careful tax planning needed. Hey, this entire stimulus has to be paid for somehow. Enjoy the new format.
Residences & Vacation Homes (applies if you: live, rent, sell, bought, gift, financed, refinanced, had debt cancelled, convert part of all of residence to rental):
Specifically, this section covers:
■Home Mortgage Reduced or Canceled
■Gain Exclusion – Sale of Principal Residence
■Residence Gain – Other Issues
■Home with Personal & Rental Use
■Homes Classified as Rental Property
■Vacation Home – Not Rented
■Converting Residence to a Rental or Investment Property
■First-Time Homebuyer’s Credit
■Energy Tax Credit for Homeowners
- Owning a House – typically allows someone to itemize their deductions (taxes & mortgage interest).
- Refinance – get a copy of the closing statement. There are likely deductible closing points, and prorated interest and taxes that may be deductible.
- Gain Exclusion – singles can exclude $250,000, married (and certain surviving spouses) can exclude $500,000. Certain tests must be met.
- Electing Out of Gain Exclusion – if first house has only a small gain, include the gain and wait for the sale of another house within two years that has much larger gain.
- Reduced Gain Exclusion – if you don’t meet the two year ownership and use tests, a reduced exclusion still may apply if the reason for selling is job relocation, health problems, unforeseen circumstances (involuntary conversions, natural or man-made disasters, death, cessation of employment, change in employment that results in person’s inability to pay basic living expenses, divorce or legal separation, multiple births resulting from the same pregnancy – many other “unforeseen circumstances” are defined in IRS Private letter rulings).
- Effect of Rental or Business Use – gain exclusion still applies if part rented is not detached.
- Converting a Vacation or Rental Property to a Principal Residence – Starting in 2009, gain attributable to a period of nonqualified use cannot be excluded (proration of gain required).
- Homes with Personal & Rental Use – allocation of expenses based on days rented required. See various scenarios below:
If personal use is more than 14 days, rental use is 14 days or less, then income is not taxable and not reported, mortgage interest all deducted on Schedule A, property taxes all deducted on Schedule A, expenses directly related to rental are nondeductible, and other rental expenses (maintenance, insurance, depreciation) are nondeductible.
TIP: Have 14 business meetings at home and charge fmv rent. Rent your children’s home for your business for fmv rent (great income shifting strategy – you get deduction, they don’t pay tax on the rent).
If personal use is no more than the greater of (1) 14 days or (2) 10% of the number of days rented, rental use is more than 14 days, then income all reported on Schedule E, mortgage interest portion related to rental deducted on shed E, BUT personal use portion nondeductible if the dwelling unit is not used as a home (BE CAREFUL OF THIS). if it is, then the mortgage interest is prorated between Schedule E and Schedule A, property taxes prorated between schedule E and schedule A, expenses directly related to rental deducted on Schedule E, other rental expenses – portion related to rental activity deducted on Schedule E, personal use portion nondeductible.
- Vacation Home – Not Rented – consider if it was used as principal residence for any part of the year because that may count toward 2 year rule for gain exclusion. Even part year use as principal residence may count because periods can be aggregated to meet two year rule. TIP: If you own two or more vacation homes, you can designate only one as second residence for qualified residence interest. However, you don’t have to pick the same one each year (i.e. mortgage on one vacation home is paid down or refinanced at a lower rate, then pick another vacation home that year as designated second home to yield larger interest deduction.)
10. Converting Home to Investment Property – if former home is not rented may be classified as held for investment. Interest expense becomes investment interest expense subject to limitations and taxes can be deducted or capitalized. Also, you can deduct properties operating expenses, but they would be subject to 2% of AGI limit, IRS looks closely at taxpayer’s purpose, intentions and motive to determine if its investment property (if you continue to hold property after its conversion, this is investment. If you try to sell property immediately after it’s not a residence, it stays as a residence. TIP: If you have owned the property as a principal residence for at least two years, you can still convert the property to investment property for up to three years and exclude gain. Also, after conversion, it can be exchanged for like kind exchange on a tax deferred basis.
11. First Time Homebuyer’s Credit – Homes purchased between January 1st, 2009 and November 30, 2009 – credit is $8,000. AGI phase out applies. TIP: You can elect to treat 2009 purchase as made in 2008 and amend your 2008 return for this purpose. GREAT NEWS – CREDIT HAS NOW BEEN EXTENDED THRU PURCHASES MADE THROUGH JUNE 30TH, 2010. CFREDIT IS REDUCED TO $6500. AGI LIMITATIONS FOR PHASE OUT RAISED.
12. Energy Tax Credits for Homeowners – A credit can be claimed for certain energy efficient home improvements or property placed in service in 2009 and 2010. Keep the manufactures certification when an item is purchased for three years (statute of limitations on your return). Summary of Personal Energy Property Placed in Service During 2009 (ALL OF THESE LIMITED TO LESSOR OF 30% OF THE COST OR $1500 MAXIMUM PER TAXPAYER): WINDOWS & DOORS, ROOFING, INSULATION, HVAC, WATER HEATERS, BIOMASS STOVE (STOVE WHICH BUNRS BIOMASS FUELS LIKE WOOD AND WOOD WASTE AND WOOD PELLETS, GRASSES, ETC.), SOLAR WATER HEATING, SOLAR ELECTRIC, FUEL CELLS, SMALL WIND ENERGY, GEOTHERMAL HEAT PUMP, ETC.
13. Energy- Efficient Credit For Contractors – up to $2000 allowed to a contractor for each qualified new energy efficient home that the contractor constructs and which is acquired by a person from the contractor for use as a residence.
14. Home Mortgage Reduced or Cancelled – exception for debt cancellation of qualified principal residence (up to $2 mil). Even if not principal residence, insolvent or bankrupt taxpayers can exclude the income.
15. House as Rental – Passive Activity Loss Exception – losses up to $25k may be allowed to offset ordinary income. AGI limits apply.
Investments (Stocks, Bonds & Mutual Funds):
Specifically, this section covers:
■Capital Gain Rules & Rates
■Taxable vs. Tax-Exempt Returns
■Treasury Bills
■Discount Bonds
■Premium Bonds
■U.S> Savings Bonds
■Stocks – Share Identification
■Section 1244 Stock Ordinary Losses
■Wash Sales
■Worthless Securities
■Stock Dividends & Stock Splits
■Investors vs. Traders
■Mutual Funds
■Investment Expenses
16. Capital Gain Rates – 28% rate on gain of sale of collectibles held more then one year, 25% rate on un-recaptured Section 1250 gain on sales of depreciable real property held more then a year (if in lower tax bracket, the lower rate applies – TIP: Consider putting property in name of family members in lower tax bracket), 15% and 0% rate – the 15% rate (0% for taxpayers in the 10% and 15% ordinary income tax brackets) applies to the sale of assets held more than one year. The 15% (or 0%) rate also applies to qualified dividends. PLANNING IDEAS TO REDUCE TAXABLE INCOME IN YEARS 2009-2010 TO GET THE 0% CAP GAIN RATE – (1) DEFER BONUSES OR CONTRIBUTE TO RETIREMENT PLANS AND IRA(S), (2) CONVERT INVESTMENTS FROM TAXABLE INSTRUMENTS TO NONTAXABLE MUNICIPAL BONDS OR OTHER TAX-FREE FUNDS, (3) CONSIDER TRANSFERRING MUTUAL FUND HOLDINGS INTO EXCHANGE TRADED FUNDS (ETFs) TO AVOID YEAR-END DISTRIBUTED INCOME, (4) REVIEW STATE TAX POSITION AND DETERMINE THE BEST YEAR TO PAY ESTIMATED TAX (FOR STATE TAX DEDUCTION), (5) BUNCH DEDUCTIONS FOR MEDICAL EXPENSES, CHARITABLE CONTRIBUTIONS AND THE LIKE INTO A SINGLE TAX YEAR, (6) CONSIDER HME EQUITY LOANS TO CONVERT OTHERWISE NONDEDUCTIBLE PERSONAL INTEREST OR STUDENT LOAN INTEREST INTO DEDUCTIBLE EXPENSE, (7) POSSIBLE GIFTING OF APPRECIATED CAPITAL GAIN PROPERTY TO DONEES EXPECTED TO BE SUBJECT TO THE 0% LONG-TERM CAP GAIN RATE IN 2009-2010 (MAY NOT LAST BEYOND THAT) – WATCH OUT FOR KIDDIE TAX RULES.
17. Capital Losses. Up to $3000 of capital losses can be deducted against ordinary income each year. Any remaining loss is carried forward indefinitely to future tax years.
18. Grouping Capital Gains & Losses – First grouped into long term and short term, and then the long term is further grouped into the various cap gain rates (28%, 25%, 15% or 0%. Further details available on how they are grouped and used, then the net remaining unused loss from the short and long term capital losses can be used up to $3000 each year then carried over indefinitely.
19. Timing Security Sales to Minimize Taxes – delay a planned sale if at a gain to meet 12 month holding period (lower rates will apply).
20. Use Capital Losses to Offset Short-Term Gains – Consider timing the recognition of capital losses for years when they can offset short-term gains rather than long-term gains. Capital losses produce the most tax savings when they offset short term gains, 25% Section 1250 gain or 28% capital gains.
21. Take Advantage of Stepped Up Basis Rules – Taxpayers holding appreciated capital assets but who have a short life expectancy either because of age or terminal illness should avoid recognizing the gain. Taxpayer’s estate or heirs receive a stepped up basis (fmv at death) and any gain recognized because of post death appreciation is treated as long term, regardless of when the property is sold.
22. Watch Out for Stepped-Down Basis Rules – adjusting a capital asset’s tax basis to date of death value works both ways. If it has depreciated, it must be adjusted down to new lower fmv. If a taxpayer dies owning property that has declined in value, the unrealized loss goes away and no tax benefit is ever realized. Therefore taxpayers with a short life expectancy should consider selling depreciated property to claim the tax loss, which may reduce income taxes in years before death. Any unused capital losses at the time of death expire unused.
23. Compute the Price to Which a Stock Can Fall & Still Be Advantageous to Hold for Long-Term Capital Gain Treatment. Very important because if you think the stock will fall in price before long term holding period is met, then you may be better off selling the stock at the current price and recognizing a short term capital gain. Formula is: Stock Price Break Even Point = Current Price – [(Current price – basis) X ordinary tax rate] – (.15 X basis) / .85
24. Be Careful if Your Brokerage Firm Allows Your Stocks to be Short Sold (Now You Know To Ask Your Brokerage Firm This) – The Dividends paid while lent out on short sale (which are known as payments in lieu of dividends) will not be qualified, and subject to ordinary income tax rates. Many stock brokerage agreements allow the broker to lend out stock held in a margin account. In the past, investors were generally indifferent (and often unaware) that their stock was lent out, since it did not affect the amount they received, and dividends and payments in lieu were taxed at the same rate. The rate reduction on qualified dividends now creates a tax cost to lending securities.
25. Taxable vs. Tax-Exempt Returns. It’s important to know if the after-tax returns of a taxable bond are higher or lower then a municipal bond. Just because the taxable bond pays a higher yield doesn’t mean its really yielding a higher rate of return after taxes are factored in. Use the following formulas to help with this determination: Taxpayer Does Not Deduct State Income Taxes (doesn’t itemize): After tax yield = Pretax yield X (1-combined state and federal tax rate). Taxpayer Deducts State Income Tax (itemizes): After tax yield = Pretax yield x [1-combined state and Federal tax rate + Federal rate X state rate)] Another method that can be used for this comparison is to determine the equivalent taxable yield of the tax exempt investment using one of the following formulas: Taxpayer Does Not Deduct State Income Taxes (doesn’t itemize): Equivalent Taxable Yield = Tax-exempt yield (after-tax yield / 1-combined state and Federal tax rate. Taxpayer Deducts State Income Tax (itemizes): Equivalent taxable yield = Tax exempt yield (after tax yield) / 1-Combined state and Federal tax rate + (Federal rate x State rate)
26. Other Factors to Consider That Affect the Analysis of Taxable Versus Tax-Exempt Investments: (1) Taxable interest increase AGI, which can reduce allowable itemized deductions or certain credits subject to an AGI phase out (2) Taxpayers who do not generate sufficient taxable income may lose the benefit of itemized or standard deductions and personal exemptions. Taxpayers may want to generate enough taxable income to take advantage of these deductions, assuming the rate earned on taxable investments is at least equal to the rate earned on tax exempt investments.
27. Potential Tax Advantages of T-Bills: No OID (interest taxable at maturity rather then over the life of the T-Bill., T-Bill interest income not subject to state and local income taxes, taxpayers can elect to recognize the acquisition discount of T-Bills as it accrues rather than at maturity or sale (this matters if you think you will sell T-Bill before maturity because if no election has been made, and gain from the sale is less then the amount of discount that would have ratably accrued to the date of sale, ordinary income is recognized to the extent of the lesser of (1) gain from the sale or (2) the amount of discount that would have ratably accrued to the date of sale. If the accrual election was made and the T-Bill is sold at a loss, capital loss results. In this case, making the election to include the accrued discount would not be beneficial.
28. Be Aware That OID Applies For Bonds Other Than Tax-Exempt Bonds, T-Bills and Other Short-Term Obligations, Series E, EE and I U.S. Savings Bonds Issued at a Discount.
29. Purchasing Bonds at a Premium (at a price above face value) & Making Election to Deduct the Premium Paid over the Life of the Bond. This offsets interest income on the bond, which otherwise would be taxed at ordinary income tax rates. Amortizing bond premium is generally advantageous because the taxpayer can offset a portion of ordinary income from the bond. Unamortized premium otherwise becomes part of the bond’s basis so its recovery reduces capital gains (or increases capital losses), which is generally less beneficial than an ordinary deduction.
30. Selling Bonds Purchased at a Premium – The sale of the bond will result in a capital gain or loss. If held long term, preferential rates could apply. Taxpayers can use a sale and repurchase to create a beneficial tax situation. This is possible when a taxpayer receives capital gain treatment on the sale of a bond and obtains an offsetting ordinary deduction for a bond that has a corresponding premium deduction.
31. Bonds Held To Maturity – if election was made to amortize premium, then it will have a basis equal to its face value, and no gain or loss will be recognized on redemption, but while holding the bond, the premium was amortized offsetting interest income (preferential). If the premium had not been amortized, on redemption a capital loss will be recognized (not as advantageous).
32. U.S. Saving Bonds Tax Advantages – interest income can be deferred until redemption or maturity on the following bonds. (1) Series E and EE U.S. Savings Bonds, (2) Series I U.S. Savings Bonds combine the features of deferring taxes on the interest until maturity with inflation protected growth.
33. Election to Accrue Savings Bond Interest. Taxpayers can elect to report interest on the bonds mentioned above over the life of the bond. This makes sense when any of the following apply (1) Additional current income may go untaxed (for example, the taxpayer’s income is below the filing limit), (2) Additional current income would be taxed at a lower rate than income in the year of the bond’s maturity, (3) The tax rate is relatively low for the final return of a deceased tax-payer in relation to the tax rate of the estate or beneficiary, (4) An NOL or other carry forward item is expiring or otherwise could be used to offset the additional income, (5) Itemized deductions are of little or no benefit because of a low level of taxable income, (6) the accelerated income is offset by investment interest expense that would otherwise be deferred until investment income is incurred.
34. Taxpayer’s Should Consider the Impact of the Accrued & Recognized Income on the Taxability of Social Security Benefits. I.e. spreading the income may create less of an impact than including all of the accrued interest in the year the bond matures.
35. Taxpayer’s Should Consider That Tax Rates are Likely Going Up. By accruing the income now, rather then taxing it all at maturity, it may be subject to a lower tax rate.
36. Transfer Bonds to Donee in Lower Tax Bracket – although taxable income is triggered equal to the difference between the bond’s issue and redemption prices at the date of transfer, gifting a bond may be beneficial if substantial income is yet to be earned on the bond and the donee is in a lower tax bracket.
37. Savings Bonds for Education Expenses – if the interest from EE U.S. Savings bonds is used to pay for a child’s education expenses, all or a portion of the interest may be excluded from income. Must be for qualified higher education expenses.
38. Swapping Bonds to Claim Losses – sell bond with a loss to create a capital loss if you have capital gains needing to be offset. Watch out for the wash sale rules (can’t buy substantially identically bond within 30 days – bonds issued by different states are not substantially identical, bonds with different coupon rates are not substantially identical).
39. Watch Out For AMT Tax From Private Activity Bonds – just make sure to ask your advisor if any “tax-exempt bonds” are “private activity bonds”. If they are, they are likely going to subject you to AMT.
40. Be Aware That TIPS (Treasury Inflation-Protection Bonds) Can Create Phantom Income. Each year, you must recognize interest and any increase in principal resulting from inflation. This is phantom income because you’re not actually receiving the increase in principal until you sell the bond. Therefore, these really may be more suitable for retirement accounts where the phantom income has no impact.
41. Stock Share Identification – Be aware that you have the right to identify to your broker which shares of stock you want sold. This could impact the gain or loss on sale as stocks bought at different times may have a different basis. Be sure this is done in writing. Otherwise FIFO is used.
42. Be Aware of Rules for Stock Holding Periods. Just be aware that there are various different rules on how long you are deemed to have held a stock (for determining short term versus long term) depending on how the stock was acquired (purchase, nontaxable stock dividend, taxable stock dividend, dividend reinvestment plan, stock split, received as a gift, inherited stock, by exercising a sock option, employer stock received from an employer’s retirement plan, etc…).
43. Section 1244 Stock – Eligible Small Business Stock – Sale That Results in a Loss is Ordinary (limited to $50,000 per year single or $100,000 MFJ). Definition of section 1244 stock should be researched further. Consider spreading the sale if these limits will be exceeded in the year of sale.
44. Sale of Qualified Small Business Stock at a Gain – Two Tax Advantages available (1) 50% of the capital gain can be excluded (60% if in empowerment zone, and even a 75% exclusion for empowerment one stock acquired from 2/18/09 through 12/31/10), and (2) Rollover of gain available if new QSBS purchased within 60 days.
45. Wash Sale Rules – No loss is allowed on the sale of a stock if within 30 days taxpayer buys substantially identical stock or securities (TIP: Sell a stock at a loss and buy the ETF of that stock to replace it – this wont be subject to wash sale rule).
46. Worthless Securities – a capital loss is allowed in the year the investment becomes worthless. Very detailed rules are applicable for determining when a stock is considered worthless (in general, considered worthless at the time it first has no liquidation value and no reasonable hope or expectation exists tat it will become valuable at a future date).
47. Stock Dividends & Stock Splits – there are a slew of rules related t whether or not stock dividends are taxable and what the basis in these new shares are. Further research should be done if you received stock dividends or stock splits, t properly account for the transaction for future tax ramifications.
48. Investors versus Traders – Different tax rules apply so it’s necessary to distinguish if you are a trader or an investor. Very specific rules are used to determine this classification. Big tax differences such as trading expenses for traders are deductible as ordinary and necessary business expenses on Schedule C, a home office deduction may be available for traders, and many more tax differences. If you are actively trading your account (you spend a lot of timing trading and do it on a regular basis, you should further research this area).
49. Mutual Funds – Determining Basis – FIFO, Weighted Average or Specific identification can be used. Must be used constantly. Can have vast differences in tax results. Mutual funds usually have dividends re-invested so this becomes important.
50. Be Careful Not to Purchase a Mutual Fund Right Before The Record Date (the date which determines which shareholders will receive a distribution). Purchasing just before the record date is buying a tax liability. This is because the funds price usually goes up by the income that is about to be paid out. Also, typically at year end they make capital gain distributions. Don’t purchase them near year-end.
51. Consider ETFs Over Mutual Funds – ETFs typically distribute little or no income and have very little fees.
52. Tax Efficient Mutual Funds – these funds turn over their investments far less then non efficient funds. Index funds tend to be more tax efficient, resulting in less phantom capital gains.
53. Consider Selling Shares of a Mutual Fund Before Distribution – in essence this converts what would be dividend income, typically taxed at a higher rate then capital gains) to a capital gain subject to a lower rate because the funds price usually increases by the amount of income about to be distributed.
54. Donate Appreciated Stock or Mutual Fund Shares to a Charity Just Before Dividend Paid – deduction is fmv at date of donation, and no capital gain is recognized. Doing this right before a dividend is distributed usually results in a higher deducting amount because FMV is higher.
55. Mutual Fund Capital Loss Carryover – read the fund prospectus to see if the mutual fund has capital loss carryovers. The fund can carry these over for 8 years and this will help shelter future capital gains that would otherwise be distributed t shareholders and taxed.
56. Investment Interest Expense – Investment interest is interest paid or incurred on indebtness incurred to purchase or carry property held for investment. It does not include qualified residence interest, interest in a passive activity, capitalized interest, interest related to tax exempt income. Investment property includes any property producing interest, dividends, annuities, royalties and gain generating property other than that used in a trade or business.
57. Investment Expense Are the Deductions Allowed (Other Than Interest) That Are Directly Related to the Production of Investment Income.
58. Election to Include Qualified Dividend Income & Net Capital Gains in Investment Income – Normally, these are not considered investment income. You can elect to include all or part of these as investment income. If elected, this income is subject to ordinary income tax rates (not preferential dividend or capital gains rate) but then investment interest expense can offset this income.
59. Minimize Expenses Allocated to Tax Exempt Income – Because these expenses are not deductible. So investment interest expense for the purchase of tax exempt income investments is not deductible. An allocation can be made using a pro-ration based on the number of transactions or time spent in each class. A statement must be attached to the return showing the allocation method used.