Just a few thoughts...If the house is spacious enough where there is no need for extra private space, I'd say keep the garage.

Late on paying rent constantly. 

Did they pay rent on time, how did they take care of the property, would you recommend renting to them, etc?  

You need budgets and financials, so probably have to pay to get that done. 

Pay attention to how your funds are handled and what protections, if any, are offered.

So much knowledge, I'd pay thousands just to spend an hour with him.

I dont mind the extra bookkeeping.

And there are ways to cure other than paying the note in full.This is a common problem these days - not enough understanding, discussion and disclosure throughout the transaction: regarding the acquisition, the disposition, with the seller and with the end buyer.I have a law and title office and we have closed thousands and thousands of sub to/wraps. 

I am looking for advice if I should just pay my taxes up front when using pre tax funds in lieuof having the IRA own the property and deferring taxes

“People” always think something they already own is worth more than they’d pay for it if they didn’t own it.