This is especially true if you're trying to buy in the best location possible.

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.'

Quote from @Robert Rixer: With on market deals like this, there are two scenarios: 1) you see something that no one else sees OR 2) everyone else sees something you don't That is true

The reverse is also true.

This is true but the answers are sometimes wrong still 

AirCover is not a true insurance policy; it only provides coverage for guest-caused damages, and even then, compensation is at Airbnb’s discretion.

Just make sure if you're paying that much for your coverage you are getting a true short term rental (commercial) policy.

@Rebecca Gonais this something that you have a passion for and want to do?  

Various industries are now starting to utilize it for true real world services. 

Short and sweet here: There are no true DSCR HELOCs.