``You are better off selling as low as you can. You lower the profit on which you will be taxed``
C`mon Paul, paying taxes isn`t the worst thing in the world, and it has skewed your logic here. Let`s assume Kirk has all free shares (no tax basis). If he sells them for $10 and pays tax on long term gains he will have $8 to put into his Roth. If he sells them at $9 to pay less tax, he will have $7.20 to put into his Roth. Sometimes you just have to pay the piper.