In real estate, you do not want to entertain a money train or issues and no profit.

You might also be a good candidate for a small boutique hotel, an operator looking to retire will often entertain seller financing on fair terms and you could likely qualify for a SBA loan to help with your vision. 

You do not want to entertain short term renters.

hammocks, outdoor entertainment options etc. are going to be your make or break!

DON'T FIND A BUYER AGENTSomeone who used to be a CBRE agent and now owns a team doing large-scale commercial investments told me to never find a buyer agent, because the seller agent would not want to entertain your offer.

Not sure if its a regulation issue or what it is, but I've only been able to even entertain the idea of doing business with HMLs on the MN side of the border. 

Investors don t invest for RE speculation they invest for cash flow.There are thousands of investors who are professionals, small business owners , professional athletes, entertainers , high 6-7 figure incomes who buy RE to benefit from its cash flow.

They had friends in town and enjoyed entertaining.

It sounds like you might already be aware of this, but the only time you can put a rental property on a Schedule C is if you provide those "hotel-like hospitality services" that you mentioned, which means things like not just cleaning between guests, but daily cleanings during guest stays, and/or providing them with things like meals or entertainment during their stay. 

Another great prep strategy is to have the building pre qualified with a local or experienced lender for potential buyers to connect with and or they could entertain a full or portion seller carry back if they want to maintain some income.