No. of Recommendations: 4
In a taxable account, you can fiddle with the timing, and sell losers at 364 days and winners at 366 days.
Actually, that doesn't matter.
When you file your taxes, loses and gains are combined and you are left with just the net gain or loss and net sort-term or long-term.
Sort term loss of $1000 and a long term gain of $1100 = net $100 long term gain.
Sort term loss of $1100 and a long term gain of $1000 = net $100 short term loss.
Would be nice if you could take the loss at 22% tax and the gain at 15% tax, but it doesn't work like that.
The only way to do that would be to lump the losses in one year and lump the gains in a different year. That would be pretty hard to do, though.