Around this time every year>, I write about strategies to reduce taxes, but this year, the uncertainty surrounding the tax code is throwing tax advisers for a loop.
For instance, say the lame-duck Congress votes to extend the so-called Bush tax cuts (probable). Afterward, the president could take out his veto pen and render the vote moot (possible).
In 29 years as a tax pro, I ve never seen so much uncertainty this late in the year.
My advice: Do what you gotta do now. Then get prepared to make additional tax-saving moves in the last few days of the year, when we will hopefully have a better handle on policy changes for 2011. Here are some suggestions.
Do What Ya Gotta Do Now: Sell Losing Shares in Taxable Accounts
If you want to sell some losing investments (stocks or funds worth less than you paid for them) held in taxable brokerage firm accounts, do it now. The resulting capital losses will lower this year s tax bill because you can deduct them against capital gains from earlier in the year. If your 2010 losses exceed your gains, you ll have a net capital loss for the year. You can deduct up to $3,000 of that net capital loss against 2010 ordinary income from salary, self-employment income, interest income or whatever. (The net capital loss deduction limit is only $1,500 if you used married filing separate status.) Any excess net capital loss is carried forward to 2011 and beyond and will generate future tax savings.
Depending on what next year s capital gains tax rates turn out to be, selling losers this year instead of next year could be sub-optimal, tax-wise. Or not. Nobody knows. What you do know is you have some doggy investments you want to dump. So dump them, and let the tax chips fall where they may.
Do What Ya Gotta Do Now: Sell Winning Stocks Held in Taxable Accounts
If you want to sell some winning investments (those worth more than you paid for them) held in taxable accounts, do it now. But keep in mind that although the gains from shares you ve held for over one year will be taxed at a maximum federal rate of only 15%, short-term gains will be taxed at your regular rate, which could be as high as 35%. So hanging on a bit longer to lock in the lower 15% tax rate on some 2010 sales could make sense.
There s no reason to put off selling winning investments until next year in the hopes that tax rates be lower unless you already know next year s income will be significantly reduced. Otherwise, I can almost guarantee the tax rates you ll face in 2011 won t be any lower than this year s rates.
Be Ready to Prepay Deductible Items (but Don t Do It Yet)
Paying more of your deductible expenditures (like mortgage interest payments or charitable donations) this year to produce higher 2010 write-offs makes sense, but only if you expect to be in the same or lower tax bracket next year. And that s only a sure thing if you already know next year s income will be significantly lower. If that s not your situation, be ready to prepay deductible expenditures before year-end but don t actually do it yet. If it becomes clear you ll face higher tax rates in 2011, you might want to defer those expenditures into next year, when the resulting deductions will deliver bigger tax savings. Here are some items you can easily pay either this year or next, depending on what happens with next year s tax rates.
* Mortgage interest included in a house payment due on Jan. 1, 2011.
* State and local income and property taxes due early next year. (But forget about doing the prepayment drill if you know you ll owe the alternative minimum tax for 2010. Write-offs for state and local income and property taxes are not allowed under the AMT rules. Therefore, prepaying those taxes will do little or no good if you re an AMT victim.)
* Donations to IRS-approved charities.
* Expenses subject to limits based on adjusted gross income. The two prime candidates are unreimbursed medical expenses and miscellaneous itemized deductions. Medical costs are deductible only to the extent they exceed 7.5% of your AGI. Miscellaneous deductions for investment expenses, fees for tax preparation and advice and unreimbursed employee business expenses count only to the extent they exceed 2% of your AGI. If you can bunch these types of expenditures into a single calendar year (either 2010 or 2011), you ll have a fighting chance of clearing the AGI hurdles and getting some helpful write-offs. (Once again, the prepayment strategy may not work for AMT victims because medical expenses must exceed 10% of AGI to be deductible for AMT purposes, and miscellaneous itemized deductions are not allowed under the AMT rules.)
Be Ready to Prepay College Tuition (but Don t Do It Yet)
If your 2010 AGI allows you to qualify for the American Opportunity or Lifetime Learning higher education tax credits, consider prepaying tuition bills that are not due until early 2011 if that would result in a bigger credit on this year s Form 1040. Specifically, you can claim a 2010 credit based on prepaying tuition for academic periods that begin in January through March of next year.
If your 2010 AGI is too high to be eligible for the Lifetime Learning credit, you might still qualify to deduct up to $2,000 or $4,000 of college tuition costs. If so, consider prepaying tuition bills that are not due until early 2011 if that would result in a bigger deduction on this year s Form 1040. As with the credits, your 2010 deduction can be based on prepaying tuition for academic periods that begin in the first three months of 2011. This assumes Congress will retroactively reinstate the tuition deduction for 2010 during the upcoming lame-duck session (a virtual certainty).
The Bottom Line
The advice above is pretty much foolproof even in the face of massive uncertainty about the 2011 tax landscape. When that uncertainly is finally resolved, I ll be back with more specific suggestions. Please stay tuned.