Let's say you could purchase an older, lower end, but almost ski in ski-out, condo without needing a mortgage at a fairly popular resort in the north east (for sake of argument something like a 2 bed at Winterplace at Okemo......). And your family would use it for the popular times (Thanksgiving, Christmas, Presidents, couple summer weeks). Would you be able to get any rental income to cover taxes, utilities, upkeep, HOA fees, rental fees, cleaning fees with rentals the other times? Or unless something is available the peak weeks its hardly worth even trying to rent it. And older units aren't popular any more? Interested to hear from anyone who does this? Do you even bother with the pain of trying to rent?