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. 

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. 

If we kept it in our name for a year, does anyone know if we will have to pay transfer taxes when we transfer it to the LLC in both our names?

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?

Though, you will be paying a bit more per month on the mortgage and you will have to live in the place for at least a year.

Some cities do require them to register and have insurance, but that is no guarantee of the work or quality.While many will fight you on this, my suggestion is to never pay up front. 

Someone like @Michael Plaks and pay them to look at your recent tax returns and your 1031 paperwork if you want an estimate of your taxes owed. 

I have a tenant that is refusing to pay the last two months of rent.