Unlike Robert K and many on this site, I judge a property based on total return.  

Managing 17 shopping centers and selecting sites for new developments is no small feat—kudos to you!

(https://www.mynd.co)One of my co-workers at my last job (pre-covid times) used to work\invest with them, so I had probably registered on their site back then.

I found what seemed to be a great property with a house for an STR and other space that I could expand for camping/RV sites and a barn that could be converted into a venue for events. 

Before buying or renting in an unfamiliar neighborhood, you should check the following two sites: SpotCrime, AreaVibes,These sites provide valuable information, including Livability Scores, which cover aspects such as crime rates, employment, health, housing, schools, shopping, and more.well, anything can happen anywhere.

There have been a ton of warning signs here on BP and other sites about the markets and how to be a smarter investor - but that is boring advice.

From the calculators I've looked at, it seems like it makes more sense very-long-term to hold on, but I'd love other's thoughts/resources (I'm not passionate about passing on as-much-as-possible to my kids when I die).From a blog post on this site about when to sell, one of the factors was when things have appreciated more than the rents in the area- but I wasn't sure when it was 'enough.'

One thing you might think of doing is having and promoting your own website to avoid the exhorbitant fees charged by the third party sites such as Expedia, Booking.com and Air BnB.  

At first, I looked at the various real estate crowdfunding sites.

Close to a cool little town, close to an area attraction, etc....Also do a search here and see how to screen guests, in addition to what the hosting sites do.... like no last minute bookings, no short stays....