Real Estate Professional status and Trade/Business are two completely separate issues. 

Readers should seek professional advice.

I’m not looking for cash flow per se, but I’d like for the investment to justify taking out of my professionally managed stock portfolio which did 20% this year. 

There's no accountability on tenant (simply fill out a bogus covid hardship form saying they cannot pay anything).Is it possible for me or some professional to do a credit report and dig up information on what their net worth is and go after their assets in the courts and the judge would force them to pay out of their checking / savings / retirement accounts?

Readers should seek professional advice.

You can find plenty of markets where nobody builds and you won't get competition but you won't get bookings either because there's no demand.It has been proven that, with short term rentals, it's the really professional hosts that make the bulk of the money (think the 80 - 20) rule.

For me, real estate was a means to an end...so that I could spend all my professional time doing what I love: helping people and renovating properties.  

Readers should seek professional advice.

Looks like a young group of professionals with not enough experience, navigating through various market cycles to produce an accurate  business case.  

Consulting with a tax professional is advised to ensure compliance and proper handling of deadlines.This post does not create a CPA-Client relationship.