You could make the sale contingent on the two POHs having a title.

I ran through the house with an inspector and a contractor to get an idea what we were in for and figured overall we needed to put about $50k into a rehab (this includes contingency $ just in case).

.) - This may also be a question for your Title company first.In your inspection contingency  you would like to review most of the above during that time, can it be provided for your review then?

Simple, sell to him, then buy.....or sell and buy simultaneous, with your purchase agreement contingent upon his purchase.

Allow it to go it's course.If the Seller accepts a buyer, then fine, let the deal go through to it's final course.If the listing expires without going into Contract AND if the deal falls out of Contract, such as when a Buyer fails to attain a Mortgage, then I can offer to buy the Property since there is no Agency relationship as the Contract with the Buyer had expired.I don't think I would want to offer a guaranteed buyout because I may need a contingency as well.Does that sound right to you?

Upon purchasing this property, I have a contingency that the city must recognize the house as a legal three family.

I just got my first house under contract and have a contingency clause stating that we have the opportunity to perform inspections for our own due diligence.

For your situation, hard money is fine, but I would make sure you have a contingency to complete, and own the property yourself if transitioning to him doesn't pan out.

No one with even a FHA loan or inspection contingencies had a chance at that one, let alone asking for financing. 

Seller  was trying to buy another house and needed her house under contract so she could remove contingency.