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Should I buy a vacation home?
In general that is a decision that depends on a lot of personal circumstances:

►Do you expect to repeatedly spend time in Aspen, Snowmass or the extended Aspen area?

►Can you financially afford the expenses that come with owning an Aspen area vacation home?

►Are you prepared to deal with organizing the maintenance or willing and financially able to delegate this task?

►Have you thought about what to do with your vacation home while you don’t use it? Is renting out an option?

►Would a fractional ownership package satisfy your needs at a lower cost?

There are tax benefits you acquire by owning a second home. This can make owning a second home or vacation home a viable alternative to renting. Last but not least owning property in a place like Aspen or Snowmass offers the likely possibility in participating in the appreciation of Aspen or Snowmass Real Estate.
I would be comfortable making the statement that nobody that bought real estate more than 2 years ago in the Aspen area has lost money doing so.
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