I did not know of this time log requirement for STRs, so as a newbie I am going back through emails, texts, phone logs, invoices, etc. to determine how much time I spent on everything.  

And not to mention no stock matches the dividend rate one can get in real estate with such low risk/volatility. 20yrs ownership, oh-yeah, cash-flow on renting it would be HUGE now so it's easily comparable to a 20%+ monthly dividend, if not more.

Those are probably the biggest questions someone needs to know to determine the feasibility of your ask.  

Keep learning and determine your long term goals.

You may want to pay an appraiser to determine the value at the time of inheritence.

This involves working backward from the final aim to determine the steps.

I suggest that you set clear goals and determine the types of properties you wish to pursue.

City has to inspect if I'm not mistaken to determine if threshold is met to where it is a tear down or rehabable.

And a SUSTAINABLE approach to rental property ownership. 

There is currently not a mortgage on the property, but due to the s-corp ownership, refinancing is not going as easily as I'd hoped.