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.'

Sloan, he seems to be knowledgeable about commercial real estate and after peering over his website briefly, it seems that he offers personalized training to people new to the business. 

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....

The requirements are often difficult, if not impossible to achieve in conjunction with other site requirements such as the setbacks and required outdoor area.

I'm exploring potential opportunities in short-term rentals (STR) in West Virginia, with a particular focus on glamping. As I'm new to this domain, I would to hire a consultant to perform some zoning and other due dil...

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

City-Data and Census.gov are solid resources, and sites like Rentometer can give you a good sense of rental prices.After that, I narrow it down to neighborhoods with strong fundamentals—good schools, low crime, and convenient amenities.

You could certainly reach this demographic, but it could also cost you substantially more than the return.For the money, your best bet is probably a dedicated website for your property with the key words that you want to convey.

We take ID's for all guests (in a website called Chekin) so would have documentation the booking guest is above 21.

For us, we only call people who have subscribed through our website and completed a form online.