I know the market and the prices of homes are relatively affordable with my current $7500 for a down payment.

Let's say I keep at my lease payments, which were tailored to be affordable at my income ability and potential.

To say it’s not to code is probably accurate, but is it safer, less frustrating?

I'm currently renting a 3 bedroom for 1750 , I have my brother paying 1k of that , I'm sharing a room with my little brother , at 25 years old you can imagine how frustrating that may be .

If you can afford to wait until you find a tenant that fits your standards, then by all means. speaking from the little experience that I due have.

SW Florida is running out of affordable waterfront properties and Matlacha has an incredible culture with branding opportunities.

At 95% LTV you could afford a $500K place (placing closing costs into the loan).However, with your 3 year exit, I do not recommend investing in the local market. 

They have an entire team handling marketing and selling/renting the units to people who can afford these units.

Nervous about no reserve cash in case of damages/accidents.OR2) Invest out of area, in a more affordable market, where I can afford a 20% down payment and hire agents, contractors, and managers to handle the rehab, leasing, management?

He's VERY GOOD and affordable.