You should consult with local property managers and find what the average DOM would be to lease your home and rental rates etc. this would be a good starting point. 

My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

Thirty years ago I started purchasing and living in properties in upcoming inner city neighborhoods that required renovation.

It really helped us a bunch as we got started a year ago.

Over time your Tampa investment will start to cash flow.

Excellent start. 

Quote from @Cade Antonucci: I am starting to grow my rental portfolio and am looking for online alternatives to hold security deposits.

Loan Closing Process & Borrower Forms: Soft quotes, hard quotes, loan application, underwriting period, standard loan forms, loan commitment, rate lock, loan closing, time to close (start to finish), etc.8. 

If I were you, I would start this way, if you are new to real estate investing.

Start small and Make Your Big Mistaes Early.