Unfortunately, relying on a "nice card" approach doesn't always ensure that tenants will vacate the property in good condition.

Borrow against it as needed for retirement and keep it as a high end rental if they want to vacate it.  

We do not have STR restrictions and the county is full of vacation properties.

We do this in Reno, NV (not exactly a booming vacation market) by sharing pictures & proximity to Lake Tahoe, Truckee, hikes, rivers, shopping etc. and other local spotsGood luck and congrats on becoming a Superhost!

I was going on vacation, so I arranged for my partner to give him half the second payment for supplies only. 

For most vacation rental areas, irresponsible people are not renting homes.

If you can hold on until the end of lease term, you can give a written notice and also send an email which would be Notice to Vacate. 

that means - no offense - anything that you can get without doing any work, or anything that someone serves up to you on a platter, or anything on the MLS - has been passed on by lots of other potential buyers.so with that said, here are my answers.0. read this thread.https://www.biggerpockets.com/forums/48/topics/1159104-overl...1. don't pick a random market. pick one you have ties to or know well or can drive to or hope to move to eventually or like to vacation in.2. do some more reading - books, forums. 

Start as a co-host and work under a vacation rental management company in the area to learn the ropes.

My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.