Either way, I always tell buyers we want to find the best deal, but you almost cant go wrong with a house hack, because even the worst house hack in town is better than the alternative, renting or buying a single family home. 

They also have a 'plan provider' branch called Directed IRA (that also deals with SOLO401Ks etc.. too)They would know the answers and if there is any alternatives for you.

It's a good alternative to long term rentals if that's your situation.

I'm wondering if there is a platform out there for handling payment and reservation outside of Airbnb or vacation rental by owner.

I know Seller Financing would be an alternative but that is difficult to come by, should  I be calling Hard Money lenders, I still want a good interest rate as I am a buy and hold investor so I need a longer term and no balloon payments.

I've literally copied and pasted your response to both the lender and attorney.This seems to have gotten the wheels churning as an alternative solution then followed:"We would set aside and hold in escrow the funds necessary for redeeming the ground rent after settlement.

Petersburg and this is forcing you to look for alternative solutions.

What might be a good alternative is to package the 2 smaller homes together and do a cash out with a commercial lender.

My alternative motive would be if he were to allow me to move in and do the repairs, and I were to be able to convince him to owner finance to me, how would the capital gains be calculated at that time? 

While the loan is interest only, it will probably be around 10% — better than some alternatives.