Anyplace you'd take your family on vacation could be great areas.You'll need a great property and to be able to stand out from your competition. 

If it's passive income, that's not landlording as you have found out.Why not sell all of the properties if you hate it and bank the money and consider other real estate adjacent opportunities like syndications and take your family on a nice vacation?

Found the forum while looking for information about Syndication as a tool to recruit Investment.I am based in the US and Mexico and currently just completed a mixed Vacation Rental Boutique building project in Tulum, Riviera Maya, Mexico.Looking forward to develop additional projects in the area which is blessed with high volume of local and foreign visitors.

This is true in most Colorado cities that have a similar provision in their vacation rental regulations. 

I have a mix of flips, buy and hold, buy and sell on contract for deed, one vacation rental, and one current apartment syndication.  

I would hit up a local flipper see who they use for vacate insurance policies.

At what point do summer vacation rentals typically start to book?

(Max vacated rents - your monthly mortgage payment) = +/- net cashflow.

I think the job would take a solid 3-4 days to complete, but the family doesn't really take vacations and I don't want to pay for a hotel for them to stay in during the time that job is done - even if they left, the amount of stuff to work around is troublesome.  

Vacation markets