Challenges?

It accomplished exactly what my wife and I hoped for: Got us taking directly (with them and ourselves) about what our broad goals were, and beyond that the baby steps that would take us there.

It's called people are lack a daisy and don't know business sense without someone walking them step by step through it.

It was also a great starter home and helped me take my first steps into real estate investing.

Challenges?

Obviously, different states and different processes, but ... in N.C. tax sales can be challenged by the heirs in court if they weren’t properly notified.

Again, in my state you have to have regained possession before you go through the steps needed to dispose of the tenant's personal property.

@Christian MorsingProbably not gonna find anyone or it will be challenging / if you have other assets you could cross collateralizeAnother option is to bring on an equity partner for that piece of financing

It is a little more challenging to break even on a BRRR in TX because of the property taxes and insurance so you might not be able to pull all your money out of the deal but I wouldn't let that turn you away.

Since you bring up condos: not only could the local jurisdiction change their laws (less likely in a high vacation area like Gulf Shores), but also any HOA doesn't step in and start trying to restrict Airbnb usage.I think the thing many people don't think about is the marketing aspect of the successful Airbnb's.