But we invested several years of blood sweat and tears to get things stabilized and learn the space before we turned them over to property managers. 

It WILL always be like smashing through a wall with your head as fists as the hammer, you will "get bloody", it will hurt, it will exhaust you, it will test you to your breaking point and beyond.

Ironically some of the best deals come from properties that once failed a perc test and are considered unbuildable for that reason alone.  

I work with a lot of MTR investors and what I am seeing frequently with multifamily acquisitions, particularly with new investors, is that they often test the property just like you're mentioning, as a way to dip their toes in the water and see what works in their area and for their personal style.

Skipping Toy Shop SchoolTo open a shop, you need to learn the rules, take a class, pass a test, and even keep learning as new toy trends pop up.

It’s like a built in test. 

@Jonathan B.Assuming you pass the "material participation" test for 2023 and did not use the property yourself (or used very little), you should be able to treat it as an STR for 2023, including bonus depreciation.  

However, after tenant moved out on 9/30/24, the pool for interested tenants was shallow and so we listed the property to test the market and ended up getting an offer at asking price within a couple days.

I do have folks that don't book because of that.That is a good thing as not understanding the distance to get places will create bad blood and cause those 2 and 3 star reviews which no one wants to see.Like @John Underwood, our place isn't cheap so we don't get the folks that destroy places.The bottom line is that you are renting out an expensive asset to strangers for 3-10 days or whatever.

Run owner reports.After testing a few apps, one should stand out for you.