(Minus the small percent of the payments they’ve made that’s been considered capital gains.)My understanding is the 60 payments they make will be split up in to interest (regular taxes), capital gains (15% usually), and principle pay down (non-taxable.).

If you don't plan to work anymore, you may want to consider the rule of 55.The distributions from the retirement account will be taxable in one way or another(now or later).You want to plan it in a way so the overall tax burden is less. 

ISO company that does creative HELOC's:I have a find with great equity in his home but not great taxable income.

I wonder if that is taxable or not.. ??

(The first $500k is currently tax free but becomes taxable 1095 days after you moved out.)It’s unlikely this price range will make a good rental, nor is it a property you would buy as a rental if you don’t already own it.

That option would be taxable to you. 

@Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: The value of a deduction depends on (a) whether you're actually able to use it to reduce taxable income and (b) your marginal tax rate.As an STR, assuming the average rental period is 7 days or less, key items to consider are: (a) material participation and (b) avoidance of "excessive" personal use.

When planning a transaction that involves conveying real property to a controlled entity, the property tax records should be reviewed to determine whether there is a gap between the fair market value (“FMV”) (from the county property appraiser’s perspective) and the assessed or taxable value (the amount on which the tax is calculated).

Wouldn’t that be sweet for stocks in a taxable account?  

First, we have to assume that you will have a significant taxable capital gain and will NOT be using tax strategies that defer this tax, such as the already mentioned 1031 exchange.