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. 

There are also online portals from many property management softwares that allow people to pay online. 

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.

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

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?

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.

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. 

Here’s a detailed breakdown of these two types of markets and the factors that contribute to each:Cash Flow Market, a cash flow market is one where rental income exceeds the expenses of owning the property (mortgage, taxes, insurance, maintenance, and property management), resulting in positive monthly cash flow for the investor.Key Characteristics:High Rental Yields: Properties typically have high rental yields compared to their purchase prices.Stable or Slow Appreciation: Property values increase slowly over time, if at all.Lower Property Prices: Generally, property prices are lower, making it easier to achieve positive cash flow.Higher Rental Demand: Strong demand for rentals due to economic factors, demographics, or local employment conditions.Factors Contributing to Cash Flow Markets:Economic Stability: Stable job markets and steady local economies that support rental demand.Rental Market: High percentage of renters compared to homeowners.Affordability: Affordable property prices relative to rental income.Local Policies: Landlord-friendly laws and regulations.Appreciation Market, an appreciation market is one where property values increase significantly over time, offering substantial capital gains upon sale, but rental yields may be lower, resulting in lower monthly cash flow.Key Characteristics:High Property Value Growth: Significant annual increases in property values.Lower Rental Yields: Rental income may not cover the monthly expenses, leading to lower or even negative cash flow.Higher Property Prices: Generally higher property prices, which can make it harder to achieve positive cash flow.Strong Economic Growth: Rapid economic growth, population influx, and development.Factors Contributing to Appreciation Markets:Economic Boom: Strong local economy with job growth and high-paying industries.Population Growth: Influx of people moving to the area, increasing demand for housing.Infrastructure Development: Significant investments in infrastructure, amenities, and services.Desirability: High quality of life, good schools, and attractive neighborhoods.I hope this information finds you well. 

I had one single mom that only had to pay $25 a month, and she was late every month!