It's hard to beat a good house hack.

How can I optimize my situation to be at least break even or, even is short term like air bnbs andvacasas reay good?

This is much much much faster and requires far less equity than if you compared that to say traditional single family rentals. 

Going after the tenant for a portion of the claim in small claims court, just to get to a judgement faster and with less of my own spent going after bad, as the tenant does not appear to have assets.

A solid understanding of the rules can open up opportunities you didn’t even know existed.House hacking can be a powerful strategy to build wealth while covering your living expenses, and incorporating advanced strategies like 1031 exchanges can help you scale faster.

I’m starting with just 1 listing but plan to recruit neighbors in my beach market to list on my custom website tailored to our community / market so I hope to be at 10+ listings soon even though I only own & operate 1 right now.Guesty’s pricing did not appear to be competitive and for someone starting with fewer than 4 units but planning to scale up behind that, Guesty does not offer a migration path from their “for hosts” product to their “for pros” version - it would have been a complete redo on setting everything up.

we manage around 40 right now (used to be at 80 or so) not my favorite program for sure but in some areas and for some homes it is the right path to take. 

The top of the chimney must be at least 2 ft higher than any roof within 10 feet.

Do you knock on the flight deck door to let the captain know that he could get there faster at a higher altitude?  

They stay longer than low income cash payers on average, but they beat the snot out of your house while they are there.