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My opinion is... If the main purpose of the vehicle is transportation look for something with a low depreciation but if the main purpose is fun then just buy what you want. One can easily spend $10,000 on a 2-3 week vacation and after it is over all you have is the memories. Money only has value if you spend it.
If you buy what you really want in the first place you won't have to worry about swapping it out in 2 years.
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