We sold our house in NY when we originally moved to Europe. We were going to buy a flat in Prague but pulled out at the last possible second when we realized that we were again moving. Since then, we have been casually in the market for an investment/vacation property. The nature of our lives is that we will probably always be renting our primary residence, as we have no idea how long we might be here or where we might be headed to next. With that in mind we've been thinking about buying a place, using it for vacations here and there, and sitting on it until we retire, at which point we would either sell it or live in it part of the year.
We had been looking at Spain and Croatia, but with the property market in the US we are thinking that Florida might be our best option. My parents have a place on the Gulf Coast that my entire family has vacationed to since I was a kid. Property prices around my parent's place have dropped dramatically in the past few years, to the point where we can afford a beach unit very close to my parent's place. I am thinking that this makes perfect sense, especially when we have kids. We could basically just take them to one place and all relatives that we would have some sort of obligation to see would come to us (since they all go every year anyway). Also, the proximity to my parent's place would mean that my dad could check up on it from time to time. I know that a lot of the condos there have in house management and rental options, so if we wanted we could probably rent it out for a few months a year when we're not there.
We're not in any rush, but what am I completely overlooking here? Like I said, we sold our house before we moved, so we've never dealt with owning a property while on another continent before. Please give me all of the PITA bits that my mind is completely glossing over right now.