BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

I think special tools are needed in this instance. 

You're spot on about security deposits being a practical tool to mitigate risk, especially with applicants who have checkered rental histories.

Pete) and have narrowed it down to finding a single family home with a pool in the unincorporated Bay Pines area or Indian Rocks Beach (note, it took a long time for me to get over my beach view condo dream in a popular area but HOA fees and restrictions helped!).

I’d appreciate any feedback on whether tools like this would be valuable or if other concerns take priority.

I think I am on a path to recovery, ready to check out the market tools to finally pick and market and find some deals!

BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

If you really don't value your agent's ability and think you can do it better, it's likely best that you 1) interview more to find one that you do trust, 2) go through the listing agent, directly, if you're that comfortable with handling your side on your own, or 3) maybe get your license so you can control your side of negotiations with the proper tools needed (MLS access with agent info, showings, contracts, tax records, uploaded listing docs like surveys, disclosures, broker assistance for questions, etc.).

For analysis, you need to identify a market that interests you using tools like AirDNA, Mashvisor, Pricelabs, etc. 

Conservative debt is a tool to generate higher returns and build wealth.