Fast forward 2 years his landlord mentioned in passing he might sell the property; I was the first person on his mind.

I personally leverage, but have a large rainy day fund. 

Personal Property coverage- furniture, lawnmowers, signage, etc. 

If the IRS has a Form 1098, they assume that the person listed on the form made the payments, and they move on. 

Non-recourse has less personal exposure, but you need a very strong balance sheet to secure this without bringing in a KP.

I appreciate any feedback.Regarding Insurance, personally I would never have someone else (A Lawyer) handle the insurance on a Sub 2 deal or any other real estate deal for me, you would be setting yourself up for failure.First of all now you would need to get a POA for the attorney from the seller, that may not be your best move.

I personally think it is best to work with local professionals with a good track record. 

The cost to repair your vehicle, and perhaps the other person's car, will be WAY MORE than the cost of the insurance premiums you saved by not having insurance. 

A more realistic expectation is 24 hours which will ensure we can arrange any repairs or corrections with a team, handle it in person, etc. be curious how this plays out as I worked for local developer for a while and developed several properties in Alexandria (Specifically old town) and while the city is challenging like any city - they were mostly realistic.

So PLEASE don’t make another huge financial decision and then tell that same person after you do it.