1. Your calculations are correct
2. Mega-Backdoor Roths are complicated. While you are correct that moving after-tax money into a Roth incurs no tax implication there are still a number of issues that can get in the way. I recommend consulting a financial advisor.
3a. Selling stocks to manage your living expenses is more efficient at a much lower tax rate.
3b. At the tax rate you have listed in question 1 you are correct.
4. A lot of things are automated in TurboTax but whether it is 'with ease' or not is a matter of opinion. You have a complex tax situation and should expect your taxes to be complicated as well. Here are the instructions for entering a backdoor Roth in TurboTax. It's not a two foot putt.
@oochillies
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