Before I blew the profit from selling my old house on two new vehicles, along with end of winter thoughts (every winter) I have often thought about purchasing something up there as well. Don’t need much land, always pictured either old and small that needed a gut and remodel, a manufactured home, or build something small myself along with a modest garage for the toys. I have however always come to the same conclusion. I’m not a water guy, and I enjoy the many activities we have down here in the fox valley for the summer, so this would be a strictly winter property. If I had to guesstimate, I spend less than $2k per winter on lodging. Let’s say I ride for the next 40 years (until I’m 68), if I spend $1750 per year on lodging for 40 years, that’s $70k. There’s no way I can pay for a property/2nd home, maintain it, and pay property tax and utilities in a 40 yr timespan for $70k or less. I also have the freedom to go to whatever area I’d like (and wherever the snow is at), with no work involved or strings attached. Sure, would be really nice to have a place of my own to call (second) home, and leave all my stuff up there, but with a blue collar career, I just can’t picture myself justifying it.