VA Loan Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

If saving 20% and building direct is worth it to you I'd recommend it.

I would recommend starting in your backyard and hone your skills if its possible, I know some markets have an extreme HCOL which may make it unfavorable in your case.

I recommend that you find a trusted or recommended Mortgage Loan Originator (MLO), who can give you options for property-based loans (mostly investment loans) and they don't use your taxes but the P&L of the property.

Would definitely recommend finding a partner who can help walk you through this if you decide to move ahead. 

I can recommend property management, realtor, vendors, if you need them.

Does anyone have suggested property management companies they've used in Florida that they can recommend I reach out to, to see if we're a good fit for each other?

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Could you recommend where I can start looking?

Quote from @Brian Hill: Do anyone have a recommendation for a San Antonio Real Estate Attorney that deals with creative financing and title work?