Fannie Mae-No Politics (FNMA)

[zzNine2Five]

If one sale the FNMA from IRA when stock price is high, he/she will pay the tax on capital gain, I get this part, but if the price down, one indeed can more shares in Roth. Basically is sell high buy low. What money is lost in this transaction? Could you advise you logic?
I talked to my Financial advisor earlier, per him, we need to pay attention on how much the cashed out IRA will add additional amount on the total taxable income, therefore could potentially trigger a higher tax bracket. $600K can bump up tax tremendously so his suggestion is to do small portion each year to minimize the tax bracket instead in one shot, per say $100K each year..