We just helped close a purchase for a client purchasing a second home on the Oregon coast. 

As the seller I would pay for the energy audit, do the analysis on the work to be done (cost vs savings) and then market the home with a prepackaged improvement contract that would meet lender guidelines (solar, EE windows, etc). 45 day close to allow for enough time to do loan and obtain permits, occupancy COE+2. 

We pay $110 per month for routine maintenance. 

I’m new to the real estate field & just recently worked with an out of state client who was going down the same route!

I heard many successful stories from my past clients that have started doing this a few years back.

The caveat with FL is that the tax laws will consider you a STR for paying transient occupancy tax if the occupancy (I believe ) is less than 6 months.

Get bids for what the renovation will cost and determine how you will pay for it if you decide to move forward.Additional questions to consider:  do you know what your unit will rent for?

I think you have to pay 100$ for reports for other municipalities. 

Ultimately I do not want to be over leveraged, stuck paying a high mortgage for extended time, or live in a home that needs work I can’t fund what are your thoughts and recommendations for how I should structure my first purchase?

All you have to know is how to buy something at the right price so that it pays for itself.