In regards to how to safeguard against vacancy, screen tenants really well and have decent reserves.

After a decent amount of strong-arming my sisters are making me essentially sell one of the houses to my sisters husband.

I would say you just need a decent escrow/title company.

I have been researching this for awhile and unless it is my own property, I understand above market rent will be needed for my goal however if I am wise and have STRs in the right location and market well, I should get a decent profit.

Just the cost of doing business.Now begins the hunt for a decent futon.

There is no financial snap shot.  

A college student looking to get in the game early I'm saving up to get my first rental but I want to give private money a shot to get it done quicker, but then again with this market I also feel I should wait.

Worth a shot. say you’ll buy contingent on the property being vacant.

With the sale of a flip in 2020, I owed a decent tax liability and also pay quarterly estimated taxes which probably won't cover the sale this year.  

I'd say save as much hardwood as you can but make sure you have at least a half decent laminate because in the minds of a tenant that can really separate what they think is a cheap unit vs a nice one which can translate directly into monthly rent.