.- It's been well kept- Between transaction costs (e.g. broker fees, transfer fees), capital expenses, tax recapture I would need to sell it for $1.9M to break even.-  At it's height (2022), it could have sold for but $2.7M. 

Does someone know a range of how much $/sq ft a parking space costs in a busy area say downtown Dallas vs non busy area? 

Cost is much higher to finance under $150000 sales price.

Memorial Day to Labor Day will pretty much take care of itself, but adding in amenities like a hot tub and a sauna will help you draw in more traffic and bookings even when there's a foot of snow on the ground.Just to touch on the LTR option, I don't know if this would get you the kind of returns you'd be looking for to even cover your mortgage, let alone cover any maintenance/capex/management costs the property might require. 

Work with the local experts- talk with local zoning officials, engage architects, and reach out to contractors to understand the cost and feasibility of your project.Run your numbers- do some forecasting and layout some financial models to project costs, revenues, and returns.Make sure you are utilizing your team- aforementioned real estate broker, financial advisor/ CPA, and lawyer and others as you go.Best wishes and good luck.

-Administrative Burden: Managing substantial services may require more administrative work and potentially higher costs in terms of time and resources.Some investors do use creative strategies to maximize tax benefits, but this particular approach of converting long-term rentals into an active business reported on Schedule C while providing substantial services is less common.

I'll incur start up cost setting up my STR; like furnishing my STR. 

It's not ideal working in multiple systems but it's the most cost effective solution we have found.

It is also a low-risk way to learn all the principles of real estate investing with very limited risk, gain experience with evaluating, buying, repairing, renting and managing a property.

Also when you transfer it to that borrower, make sure in your price you include the cost it is going to cost you to give that borrower a title policy.