Q: I plan to retire in a couple of years and am strategizing my money options for maximum gain. Therefore I am allowing myself 12 years to roll over as much money as possible from 401k and 457 to Roth IRA. I am targeting to keep my income below the $250,000 threshold for married filing jt. I want to pay the taxes with my taxable account. I will have to sell LT appreciated stock. Does the sale of the appreciated stock count toward the $250,000 threshold? If so, then I suppose I will have to start selling off my stock now to bring up the cost basis in time for retirement when my income will ramp up due to the conversions.