As far as your primary residence, if you have lived in it 2 out of the last 5 years, you should not have to pay taxes on capital gains (difference between what you paid for it & what you sold it for) up to $250,000 if you file your taxes as an individual and $500,000 if you file jointly with a spouse.Just a disclaimer, I am not a tax professional.

@Caryn Fischer You can sell your house to your child below fair market value (FMV), but the difference is treated as a gift.

During my time away, I’ve explored different brokerages to hang my license, and I’m proud to share that I’ve now opened my own firm here in the Bay Area!

Probably an easy fix that might make a big difference.

I guess the different strategies FOR ME would be.A- Find a lender that would actually do the refi and pay the tax.B- Sell a property and use those funds to lend as they would go back to the IRA. 

You can take any proceeds tax free and roll into a different investment. 

and split the difference?

I wanted to get different thoughts on potentially using seller finance to handle this deal.

How long it takes to be financially ready is different for everyone.

the cash flow you are referring to, are you attributing that to the $900 difference between the PITI and the gross rents?