You want to stay in the loop, know what's happening at your property, and address any concerns pronto.

However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.

-TylerTyler, that would concern me.

Condos are cheaper than houses, and to my mind, a vacationer wouldn't care much about staying in a bigger place for their short stay, and would be more concerned with a good location and a nice view.Thoughts?

While OOS investing can be very challenging due to unfamiliarity with the location, building a team of professionals that you trust can help to alleviate those concerns.

Quote from @Celli Mowery: Hi Jamesinteresting message -I know I’ve seen your name often on the Bluegrass Investors GroupI have spent the last 5 years investing in London and while some of the concerns you mentioned did exist when we started I’m finding we haven’t had issues with tradesmen coming from Lexington & Richmond for us in recent years.

that's a huge concern of mines now

They are more concerned about protecting the hotels. 

The problem (as you have cited) is trying to understand what you need (you don't know what you don't know), where to get it, qualifying its source(s), and the validity and usefulness of all that.Pardon me if I've gone into this too much, but I meet many people with the same concerns that you are voicing and this is offered, as much as possible in direct response to your post.Please feel free to contact me if you have any comments or questions. 

The red flags of managing from a distance and hiring a property manager are legitimate concerns that make it more challenging.