Most are traveling professionals needing an alternative to a thousand dollar a week hotels.

But there are alternative exits that still profit a decent amount, in my opinion anyways.So, this is what you would call a high risk strategy? 

Over time, I’ve accumulated more cash reserves and don’t need as much flexibility, but I’m actually in the middle of a refinance right now using an interest-only mortgage—because the pricing with the lender and the corresponding ARM is more favorable than a comparable principal-and-interest loan.The key with these alternative or "exotic" mortgage types is that you need to be financially savvy and have a solid plan.

@Steve CrispIf you meet the material participation guidelines and qualify for the short term rental loophole you should get a free cost segregation estimate to see how much you would benefit from the accelerated depreciation. 

I would recommending looking at your property through the eyes of the NBA, or Next Best Alternative, to see if there is a market for you property as a mid-term rental. 

The alternative is to set up a self-directed IRA, or better, a truly self-directed Solo 401k plan, invest in alternative assets, and then do the conversion.

Are there any red flags I should watch out for when dealing with buyers who propose alternative arrangements like this?

For what the course offers, the price paid does not correspond with the value the material offers.

However, I do not know who this could be beyond a property manager which would not work in my case since I am looking to self manage for both tax (material participation in STR loophole) and profitability reasons. 

Each individual owner can have their own Deferred Sales Trust:, the assets of which can be managed to each taxpayer’s own individual risk tolerance and preferences. 4) A 1031 Exchange alternative or rescue- Unlike a 1031 Exchange, the proceeds from the sale do not have to be invested in “like-kind” property in a very short timeframe to achieve tax deferral.