Thoughts on my Plan?

[pb4uski]

...I like what Pb4uski suggested about the Roth conversions with the proceeds and withdrawing the same amount from after tax, but doesn't that produce a double tax and risk raising your tax bracket? You have to pay the tax on the conversion and then the same tax again on the capital gains from selling VTSAX.
I'm obviously not a tax professional and I'm sure I'm missing something here.

It wouldn't be double tax since the tax is on the gain and not the proceeds from the sale plus the tax rate would be capital gains tax rates which would most likely be 0% or 15% depending on income.

So if the gain was 30% of the proceeds and the capital gains tax rate was 15% the the tax on the proceeds would be 4.5%... but if the capital gains tax rate was 0% the tax would be 0%.