In the latter situation (where I am paid monthly), as a short term lender, I only do 12 month Promissory Notes.

Hello BPers,I am an investor investigating the eastern Michigan market for flips, short term rentals and buy and holds. 

But the short answer is this:   You're on the right path. 

Another big question is, do you want the headache of self-managing a short term rental?

The other is a full day drive, or a short/cheap direct airplane flight and we have family that lives nearby. 

I’ve also taken out short term loans (1-5 years) to use as my 25% down payments.

It’s a long game so worrying about the short term is kind of pointless.

and whether these would be short, medium, or long term rentals.

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.

He is the best and sells nothing.Your idea makes sense, but as you've seen with regulations, it won't work in practice for a short-term rental.I like @Dan H.'