Like @Patricia Andriolo-Bull, I hate the do you know who I am.

We have a potential buyer of a lot in St Augustine, FL who would like to build a new single family short term rental.

I do understand that the answer likely varies depending on location - this is in a very nice suburb of Philadelphia. 

We like to laminate our Design Boards and post them somewhere that everyone will see them in each room.

Then talk to a qualified, professional QI like @Dave Foster.

We ran numbers across several probabilities and it seemed like a safer bet when we purchased. 

However, alternatives like a Self-Directed IRA (SDIRA), a 60-Day Rollover, or a Roth IRA Conversion can help you avoid penalties.A SDIRA allows you to invest directly in real estate while maintaining the tax advantages of your IRA.

If you don’t like it, you can always pivot and sell, convert to a long-term rental, or move into another investment strategy with the equity and knowledge you’ve built.Starting this way means you’ll go through every key step: finding a deal, securing financing, managing tenants, and understanding property operations, but in the lowest-risk way possible.

Feel free to PM me if you'd like. 

Sounds like you're already moving in all the right directions.