OR potentially a lease to own option.

Tip: Take a couple videos of the place fully furnished before anyone moves in and send them as video tours to potential tenants on FurnishedFinder when they ask to see the place.

Start by formalizing a lease agreement, evaluating potential renovations to maximize rental income, and deciding on a rental strategy (short-term or long-term).

Why ask: This helps you understand how many people have succeeded under their mentorship, giving you an idea of the potential outcomes.

If you see at least a few zoned in the designations you mentioned above, that's potentially a good sign that you can get support from the local Alderman's office, and approval by the ZBA (zoning board of appeals), to rezone.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

A second STR in a market with year-round cash flow potential might balance out your portfolio and give you more consistent income.

In terms of maintenance, they are generally safer because you are not responsible for the exterior and common areas and potential leaks, etc.

To succeed, focus on properties in high-demand neighborhoods like Pecan Grove or Aliana, and ensure your cash flow analysis accounts for high property taxes, potential HOA restrictions, and flood insurance costs.

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and there's amazing appreciation potential.