Not sure this is necessarily a strategy, but more of an idea/dream I was thinking about the other day.
It all started because I used to live in Vail. I love that mountain! I love to ski! I live in Park City, UT now, but the weather has been horrible, so we've had very little snow (up until this week, hooray!) I so miss Vail, and thought it would be fun to go out there several weeks every winter, even every other week or something. What if I bought a vacation rental and rented it out weekly, but only 2 or 3 weeks out of the month, and then I stayed in it the other times?
I also used to live in Mammoth and have a lot of friends there. I have plenty I could rotate through crashing with so as not to wear out my welcome if I visit, but what if I did something like a part time vacation rental too? Eventually maybe do the same thing in other places, and be a real powder chaser. Own condos/homes in Vail, Mammoth, Jackson, Telluride etc.
Obviously the goal wouldn't necessarily be stellar cash flow, I'd get a lot of benefit out of using it myself. Cash flow sure wouldn't hurt! I was just thinking though, that timeshares cost money, renting a place on vacation costs money, what if I owned places and made a little cash flow? Broke even? Would this be more likely of a profitable scenario if there were multiple locations involved, as each property would be rented out a higher percentage of the time?
This could be a totally asinine idea from an investment standpoint. But even if it loses money, I really like the idea of being able to go to Vail and ski there every other week while still living in Park City. Let's just keep it simple and start there. Will this work, at all? Is this a horrible investment idea and I just need to be rich enough to live in multiple places and travel wherever I want? :)