Originally Posted by crank
There have been 2 times in my life I have semi seriously considered buying a ski condo. FIrst was Park City back in the 70's when the place was growing like crazy. ( I would have had to get my father to put up the down payment and sign for the mortgage though and he was not a skier so it would have been a real hard sell.) The second was Okemo's Solitude condos when they were first building them. The offer was 20K down on 200K for a 2 bedroom condo. Similar unit listed now for 540K. I would have done OK with either property but are there still opportunities like that in this world?
I think so. As I mentioned, Winter Park seems to be one of those. I've seen very nice condos sell for very little. I remember in 2005 there were some brand new 2 bedroom units about 3 minutes away from the slopes that were selling for $150k. In most ski town markets, property values dropped by very little, if at all in the recession, because in general the richer you were, the least you were affected- and most folks looking to buy a second home in a ski town are pretty well off (and probably aren't the type of guys in this thread talking about how many cosigners are needed on the mortgage to buy the ski-town condo...).
If you can afford to buy it, long-term a condo at a destination resort is probably going to be a pretty great investment. But that is different than needing to cash-flow and cover the mortgage, maintenance, and HOI with rentals. If you can't truly afford to pay the mortgage payment and expenses out of pocket, you can get bled white in a low snow year when you can't keep the place rented and everything breaks (and if you buy a place and rent it, this will happen).
It is kind of like Blackjack- you have some of the best odds to make money (which yes, are just shy of 50/50, it is not a perfect analogy), but you have to have pockets deep enough to not get bounced off the table when things swing in the dealer's direction.
I also think seasonal rentals can be very profitable, but if you are relying on those, you better have a very attractive property very close to a destination ski area, and you better hope a more attractive development doesn't pop up that eats away at what you rent for. Generally the places that can be expected to pay a year of mortgage payments through 3 months of renting are not budget-type places.