After five years, I am willing to buy the other owner out or they could stay in and continue earning and enjoying the property. 

Is it worth buying vs renting given I'll be staying there for 3 years.

Investors normally get there payments on time, most of the tenants stay for long periods of time because if they move it is a hassle for them, and since section 8 requires that the property stay in certain condition it will help keep the maintenance costs down. 

Personally, all of my units are full and have stayed full, no one is even late with rent much less behind, and no one is moving.

From my understanding you would have to sell the property as a business...a resort style destination with a number of amenities and places to stay.

I bounced around the minors in hockey and I wish I still owned all the places that I stayed.  

It also has the benefit of being local which is great training wheels as you learn how to be a killer host.Now assuming that you mostly want a cool property to stay in sometimes near water and don't want to spend a ton of time managing I really like the outer banks in NC.

We haven't yet, but I would think even for $300 a year it would be worth it for just one stay!

Those details can ensure your projected $25K profit stays on track. 

One of the condos where we stayed for years came out with a ridiculously long breed ban list.