As with all such views, you may need professional tax advice on any of these moves. Your situation is unique -- everyone's is. With that said, here are some things to consider in the closing days of 2012:
- Take taxable gains now. Capital gains taxes may remain where they are, but if Congress does not act they will rise -- a lot. If you intend to take the gain sometime in the next year or so doing it now will lock your capital gains rate. Note that even if you like the position this is not necessarily a lose; the "wash sale" rule only applies to losses! What this means is that you can sell a position that is profitable, book the gain and the tax liability, then immediately buy it back (less the amount you will have to send to the IRS.) This does not trigger the wash-sale rule since there is no loss being carried back. This can turn into a double-win if the stock declines in value in 2013 and you later book a loss, since losses are direct offsets against gains (and can be carried forward indefinitely for those who have not declared mark-to-market status.) Normally you'd be nuts to book a gain, crystallizing tax liability and then re-buy a position, but this is a special circumstance where it may make sense.
- Be very careful with hedging strategies or crystallizing losses that are sometimes smart across a year-end boundary in taxable accounts. Legally avoiding the wash sale rules is not all that hard; the trick is not to re-buy a losing position in "like kind" within 30 days. This is only of actual impact on tax liability across a year-end boundary (but the record-keeping is a bitch all the time.) If you trade short-term you either pull your hair out or you use something like Gainskeeper, and know exactly what I'm talking about. The exact definition of what fits as "like for like" is a matter of some debate but out-of-the-money options usually are not going to qualify as a like-for-like (deeply ITM options probably will!) In addition crystallizing losses to offset gains is sometimes smart and rather common but if you think the gains rate is going higher next year the offset is worth more in legally-avoided taxes next year than it is this year. If you have a $100,000 gain in a security next year and the capital gains rate is 25% but this year it's 15% then having a loser that offsets that $100,000 is worth $10,000 more in lawfully-avoided taxes next year than it is now! As such you may wish to consider not selling that loser until after January 1st this time around if you have taxable gains you can offset. The other side of this is that if you don't have taxable gains you can offset then booking the loss now gets you a $3,000 offset against ordinary income and carries the rest forward and it's unlikely to be worth less next year than it is now and may be worth more. Carefully consider the likely impact both ways before making your choice -- this gets complex when you have both gains and losses you can book and much depends on what you think your P&L will look like next year. Yeah, I know, it's a guessing game. Welcome to our wonderful government's idiocy.
- If you own a business and need capital equipment next year, and have the money, buy it now. There are Section 179 and related deductions that are due to expire on December 31st; if not extended they will revert to standard depreciation rules. Forcing things onto depreciation schedules doesn't matter in many cases but in high-tech businesses it hurts bad, as many things become economically worthless far before the IRS schedules say they do. Cash flow is not only King, it's God in a small business and forcing you to dribble out the capital impact of something beyond when it earns you money just plain sucks. Anyone who's ever run a technology-based business big enough to run into this problem knows all about it and has sworn up a blue streak as a consequence. Take advantage of these opportunities.
- If you are expecting an early refund, better make alternative plans. This is the 900lb gorilla in the room; if there is no immediate resolution the IRS will not be able to process returns, especially if the AMT remains unpatched. Oh, speaking of which, that's the real nasty in this deal -- the AMT. This is a Tax Year 2012 problem, not next year. It has the potential to screw tens of millions of middle-income taxpayers and the worst impact is in high state tax locations like New Jersey, California and New York. Those of you who live in those states and put Obama back in office get to thank him for this one if the AMT is not patched by December 31st as the cornholing may extend down to $40,000 AGI! Effectively what happens is that if you get hit by the AMT all your deductions off AGI go away -- for those who have high state income and property taxes you will get rammed. As someone who has had to pay this damnable tax in the past I'm chuckling at all of you who think that "taxing the rich" is an answer -- Mr. Firefighter and Ms. Teacher, you are going to get hammered on this one. How bad is this? It will turn your $2,000 refund into a zero, or worse, turn your $1,000 refund into a $1,500 bill! Thanks Barry.
In short the year is almost over but the considerations just got very real for most Americans, especially those in high-tax states. Once January 1st rolls it's too late to do any of the things you can do that will help, so consider them now, once the eggnog wears off.