Wow, you do have a rather unique situation.
I'm on the other coast of Florida, so I can't help much with Tampa area, but here are a few thoughts about the investing aspect.
Real Estate investing to become financially free takes time. Don't rush it or you'll end up buying bad deals. Analyze the properties carefully. My recommendation would be to find properties with a 100% return on capital gain (minimum) and a minimum of a 10% cash-on-cash return. I recommend this because you're building wealth at the same time you are building cash flow. Some invest only for the cash flow, I prefer the best of both worlds. These deals are not always easy to find, and you may have to analyze a large number of properties before you find one that makes sense. Don't get discouraged through the process, it WILL take time.
Build a team of people you can trust, and even when you trust them, always run your own numbers to check on everything. Though I am licensed and consider myself pretty good at what I do, I set up a series of checks for my clients so they know they're getting a good deal. I recommend that not only do they get every property inspected, but also get two or three repair/make ready bids on each property, at least a desk-top appraisal by an independent appraiser for the ARV (don't go just on what I say, pay the $100 to the appraiser to get another professional opinion on that ARV). Overall, double check EVERYTHING at every step through the process and get as much done as you can during your inspection period so you can back out of a deal and get your EM deposit back if needed, with the lease amount of hassles.
Don't rely on properties increasing in value (speculation). That got a lot of people into a lot of trouble when the market turned this last time. If you start working with an agent who says anything like "in a couple of years, it will be worth a ton more" RUN - DO NOT WALK- away from this person. They don't know how to work with an investor.
Be careful if/when you work with wholesalers. I've seen many wholesalers inflate after repair values to astronomical heights to entice a buyer. Some are reputable, but many are not. Stick with your checks and balances to ensure you are getting a good deal.
Leverage as much as you can. I'm not saying go for 100% financing, but do use other people's time, knowledge and money for as many deals as you can. Yes, it may cost you some money, but if the returns are high enough after the costs, it's worth it.
You mentioned the property you have in Ocala is in a 55+ community. My recommendation would be to not purchase in these communities (HOPA communities). You're restricting not only the pool of tenants for these properties, but also your exit strategy. If you don't have the property rented at $750/month, contact an agent in the Ocala area and ask them to run some rental comps for you (preferably in the same complex). There are usually only three reasons a unit goes vacant for any length of time: Cleanliness, condition, or price. Make sure the unit is clean, in great condition and priced appropriately for the area in which the property is located.
You are wise to stay close to your home base to look for properties. My thoughts have always been that your properties should be within a 1/2 hour drive from home or work. I have had some clients go further out, but if they're too far you'll not be happy when the toilets need fixing, or driving for 2 hours to show it to a prospective tenant.
Manage your own properties until you have at least 10 properties, then maybe consider hiring a property manager. If your properties are in excellent repair when you first rent them out, and you check everything between tenants you shouldn't have to do much other than collect your rent each month. Again this goes back to cleanliness, condition, and cost.
Once you have acquired enough in capital gains through your properties, you may want to look at multi-family properties (think 50 units, not 2,3, or 4) that you can reposition in the market...but that's a discussion for a later time.
I'm rambling on here, feel free to message me if you'd like and I'll be more than happy to respond.
Best of luck to you!