I am targeting Cincinnati, OH as potential first market because I grew up not far from there and have at least some connections.

-"analysis paralysis" is mostly a made up nonsense phrase intended to get people to go ahead and buy real estate even if they aren't ready to do so. 

Simply have the tenants sign the new lease AND have them provide you with the additional $100 BEFORE you sign the lease yourself.

If you end up at out-of-state but have capital, you likely be on a turnkey solution.If you are starting locally, that may be wholesale, brrrr, flip, buy-and-hold, (STR, MTR, LTR), and more. 

Kudos to you for doing something to create a secondary income stream. there are 5 income streams in RE rentals, possibly six if you do things a certain way.The reality here is your model (buy box) is suffering from too high an entry and too high a cost of capital.

You didn't mention the higher Florida insurance costs. 

Should I set up a trust first, then move the LLC and properties into it?

Go to Dennis Block's FB page and sign up for his webinar Friday at 10:00.   

Think of vehicles like the cyber truck where you need to sign up ahead of time to pre-order and so many people want it that the value increases shortly after they are released.

Keep it up, and look forward to the next 1,000!