In short, you ride the 'coattails' of the previous owner's taxes for the first year.  

I just keep using my rental cash flow to pay off these short term loans.

You can protect yourself with a short contract period.

Long story short, it has been over a year and the project remained incomplete and he walked away with the money.

An easier route would be to convince him to go in on the short term rental together in a partnership. 

On the other, the prospect of short-selling the homes didnt look so awesome either.

I’m also open to exploring short-term rentals, private lending, or passive investing in funds—anything that maximizes returns while keeping risk and time commitments manageable.For context, I’d consider leaving my job if this could become a full-time venture that surpasses my current compensation (low-mid six figures).

I’m currently exploring the Short-Term Rental (STR) market in Ft.

Real estate transactions, especially flips, come with specific tax implications such as the potential for dealer classification, short-term capital gains, and cost allocation for renovations, which can significantly impact your tax liability.

While short-term rentals in areas like Kissimmee, Florida, can pay for themselves and offer lifestyle benefits, the ROI typically doesn’t match what I see from my traditional portfolio of long-term rentals in North Texas.That said, short-term rentals can still be a great choice, especially if you're drawn to the area and the opportunity to combine personal use with investment income.