Greetings,First possible investment opportunity: Just looking for some wisdom here as this is a little out of my expertise on how to calculate. Looking to see if this might cashflow, or any wisdom from someone who may...

You need to make your stay unique.

The more info you can give to your guests and the more transparent you can be about all the different and unique aspects of your property or hosting style will pay you dividends. 14 - Dishwasher!

There is also a group of renters who are looking for a unique experience.

Make your property unique. 

No comps means you are buying a "unique" asset, or taking a huge pricing risk in current market.

It's a unique facility that serves functional activity such as YMCA.

As others have mentioned on here, every person's tax situation is unique and answers are not easily given over the internet and can often be incorrect. 

for a unique deal like this they might be more open, considering finding funding isn't as straight forward. just also be sure you have a backup plan for this property... what if they don't renew their lease at the end?

If you walked up to Michael Jordan and said, "I want to learn sports" he would walk away.