So even if you had a buy out agreement negotiated up front and execute that buy out agreement, the bank would still require him to be guarantor unless something drastic changed on your side financially.The best scenario here would be to purchase and rehab the property using a hard money lender or bridge lender.  

Hard money for acquisition and I financed the rehab myself.

They loved it because they got some play money right away and steady income each month without having to deal with toilets and tenants.

Just so you know, Vrbo and Airbnb will not allow you to receive an inquiry through their platforms, and then take the booking off-platform, they want their cut of the money. 

I could get the same or higher overall ROI by putting my money in an index fund which is 100% passive.Deal #2This seems like a good deal to me at the asking price.

We only needed to pay earnest money and a portion of the closing fees bring upfront investment to 12-15K.

It also depends on how much money you have and how you use it.

Cash and Hard money How did you add value to the deal?

With it being that risky, the least I could do is have some money saved up.

You should consider private money!