Az condo gives me time to spend hiking/biking during the winter. Plus the value of my condo has not depreciated anywhere close to what my portfolio has. Our condo carrying costs for 2008 were $8185. I understand that I could take those $ and just rent a place, but I'm happy with the purchase so far. I may change my mind and sell it when I get old and travel becomes difficult.
Despite my frequent lament about the AZ summer heat, right now it is just beautiful. I just came back from a walk. It's nice and cool at 65deg.
If you have the dough to park it in a condo, the annual expense of $8K is not too bad in my view. I do not include my houses in the portfolio, but I can see how one can rationalize the 2nd home condo purchase as part of the portfolio, because you can sell and "convert it to food" if you need to.
If you hold it for enjoyment for 10-15 years, and don't expect to make a killing, it's not a bad way to go. In fact, buying at the right time, you may recoup some of the annual cost when selling, if not make some profits. If you really like the locality, want to return year after year, it's the way to go, in my opinion.
Comparing owning to renting, I think it is like staying in a hotel vs in an RV. Some people like a sense of permanency, of sleeping in their own bed every night. Renting to test the water is always prudent of course.
Though the OP talks about staying on the Eastern seaboard, because meadh talked about fractional ownerships I would second that as an option.
Recently, visiting Victoria BC, we stayed at the Westin Bear Mountain. This resort also has fractional ownership condos. As Victoria, and really all of the island, is such a nice place, I found the fractional ownership an intriguing idea for US residents of the SouthWest to seek refuge from the summer heat. Unfortunately, we did not have time to talk to the sales office to see how this fractional ownership works, such as how many weeks one has, and if the time slot is fixed from year to year.
And by the way, I wouldn't mind living in Victoria year round, since the winter normal low is only around freezing. Fractional ownership works better for US citizens, since they kick you out every 6 months anyway. We did look at the window postings at an RE sales office in Sidney, and found that house prices weren't bad compared to places like SanDiego, and are in Canadian dollars yet.