I also wonder if some hosts only list during football season and then transition to mid-term rentals (MTRs) the rest of the year.New Tax Changes Coming in January 2025Starting January 2025, Airbnb will automatically collect and remit the 5% tourist tax for Gainesville.

In that case you might save taxes building with them.

This has driven up the property taxes there. 

You have the ability to sell while limiting your capital gains tax because you lived in 2 of the last 5 years. 

That means creating a clear budget, forecasting cash flow, and maintaining a detailed financial model that tracks both the current and future performance of your portfolio.Tax Optimization & Risk ManagementBeyond financial clarity, strategic tax planning and risk management are essential to safeguard and grow your real estate investments.

The challenge for a PMC is having the time to answer all your HUNDREDS of questions and handholding you as you learn, while still making money.

However, this means you’ll need to comply with the annual filing, franchise tax, and reporting requirements in both states.

They don't require employment verification, income or tax returns.

What paperwork should I keep a paper trail of to make things like taxes and other situations better/easier for myself?

If you are taking the tax write off, you are acknowledging you are paying the debt.