OP was clear that he is currently house hacking and renting out a couple bedrooms to some Navy friends.We have to contend with IRC Sec 280A. 

I would contend, in layman's terms, that the plaintiff (the alleged real estate investor 'conning' the plaintiff (owner of the claim to excess tax from a sale)) would not have succeeded in financial gains except for deception and practices considered against public policy. 

I've been using the same lease form for over 20 years....modified here and there over time to contend with situations that came up.

Asking if there is a "ceiling" so we don't contend with or create any discrimination issues? 

We have land improvements to contend with.In my example, I subtracted $25k land improvements from $40k land, leaving only $15k for the "true land."

You'd be able to tell the contenders from the pretenders.

I contend there are three things every investor needs to consider.1) Where people workWill a city lose its economic driver as workplaces start to go partially or fully virtual and let their employees live wherever they want?

You also have to contend with the condo association, which doesn't take kindly to rampant partying. 

@Meir Brach I contend that Rockland Co is NOT upstate (except to those living in NYC that has never been north of the Bronx, lol).

Generally banks move more slowly than brokers as they have more red tape to contend with.