If at the end of the trip their experience is not good, that is definitely a problem WE need to fix.

We're leaving next week for a week long Costa Rica trip with no money into the flight and a nice resort stay.

One my last trip I looked at a set of properties that were maybe 2 blocks from a Starbucks (a newer Starbucks going in is usually a good sign for the future) but my agent also tells me "well, it's kind of known that you can buy drugs somewhere in these group of triplexes".  

I have stayed there for golf trips for 5 years, so I was very familiar with the resort and location.  

We've already felt the sting ;)  My wife is there this weekend on our 3rd house-hunting trip. 

I need to take a trip back and see how much has changed since I left!!!

Make sure you schedule trip so if you get a bad vibe in person, you still have time to call / meet another company.One of the things I would check on is how large is the PM company so if the person taking care of my property goes on vacation or get sick (hopefully not), they can seamlessly back fill; Service calls have to done promptly, rent has to be collected, leasing tours have to be scheduled, emergencies have to be addressed.

Boats are a hole in the water, I've owned a few small sailing yachts, and am a ASA certified for sailing across internal waters in my past life...

Possible cash flow of about 50k annually and a ski spot for a few trips.

I would really recommend you taking a trip out here.