The trade off course for STR route is more management/cleaning of guests coming and going/risk of no bookings vs not needing to deal with long term renters months at a time if that once they move in.

However, don't have any of those loans anymore (most paid off).The only thing I do that you don't, is use trusts, and love them and they have saved my bacon a number of times.When you said all those loans have paid off, are you utilizing other methods than Sub2 at this time?

@Hunter Duplantis what @Gino Barbaro said is exactly what I was going to suggest.When you have vacancy is the time to experiment and apply your original thesis.I’m not trying to play Monday quarterback here but, you should be highly confident in where the rents should be well in advance of having a vacancy.That being said, after confirming competition rents on websites (I’d also recommend Craigslist and Facebook marketplace), you should be in alignment there.  

We purchased our second property in August 2024, a townhouse this time, in Odenton, MD.

You are missing my point on taxes.Scenario 1:  Your partner buys the house at the same time you put your cash in.  

I'd be happy to talk w/you on the phone and maybe meet some time for coffee. 

Are there any unique considerations or red flags you look for compared to the traditional rental process?

Then start analyzing deals so you get comfortable with that process.

And using the process buy a new property or properties that you also intend to hold for investment use.The issue for you might be that you purchased this property with the primary intent of selling. 

Its a a matter of time until someone does it!