You have to have a strategy to prevent these things...and I would think you don't always want to leave that to third party property management, that you want to do that yourself.Probably in most cases if you're just going a few times a year, and you're going in peak season, probably cheaper in the long run to rent hotel rooms or other STR vs buying one if that is your motivation.

@Carson CampbellThe lack of communication on their part is annoying, it the norm for a couple tenants I have though.

It works best in suburbs that allow the most unrelated parties and reasonably-priced homes such as Arvada and Lakewood. 

How can you ensure (in a contract) that both parties receive equitable stake in the property?

It's not on the water, but walkable to  a beach and part of a HOA with marina (no deeded slip but access to boat ramp).

Both parties sign, both parties keep a copy, and life goes on.

A friend of mine wanted to host a big summer party for a large number of friends and had to cancel it when he found out he needed consent from all neighbors. 

Yes you'll have more cash flow, but there are way better ways that you can accomplish that other than paying off the property.My wife and I are actually in the the same boat, we did a live and flip and are in the process of going through our next steps.

Insurance means a 3rd party may pay out.  100% different things.  

@Andrew Cowles, a very good question.In my state, and your state may differ, the upset price is an "unofficial bid" by the moving party.