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Your question is a very legit question.
1) Storage is very hard on cars. Even if it's climate controlled. Things dry out, things deteriorate, fuel systems rust, bushings go. I know, as I have stored cars. And putting them back into roadworthy operation takes a lot of time.
2) When a car is in storage and you're into other things in your life (other cars, other hobbies, family, a house, etc) time slips by very quickly. The car you put into storage sits for a year, then five, then ten. Then maybe you're over it. Maybe not, but it's another whole thing to do it all over again.
3) An '86 is the most plentiful year for the aircooled 911 if I'm not mistaken. This was the ultimate sale year. They made a lot of them, and I think it's the year that they imported the most in the history of the aircooled 911 up to that year. People used to laugh at mid-year 911s - and they only imported maybe 1/3 of those compared to a model year 1986. Not to say a 1986 is not desirable, but they are around.
4) A modern Porsche is a good idea. Personally I would not do a Boxster, but I really like the Cayman. But it's what you like.
5) I'd sell. It's amazing how fast you get onto other things and how quickly you forget about old stuff. I am one sentimental bastard and I have yet to regret selling something when I went onto something new and different. It would be harder to sell if you weren't replacing it, but you are, and you'll have fun with that one too.
Time is very valuable and life is short. Taking time to store, pay for storage, pay for new tires and every single thing in the fuel system and most other things is a time consuming ordeal. The guy who I bought my car from 'thought' he was still going to drive his 911, but twenty, yes twenty years passed and it really needed work then. It was a running and driving car, and life happened. And now it's a lot of work for me.
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