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For $10k, would it be worth a trade up. Right now, I have a 2000 Boxster S, but have been seriously considering moving up to a 2000-2004 911 Convertible.
Will I notice that much of a difference in performance?
Also, in terms of status and perception to the general public, is there much of a difference?
Depends on where you are, in northern California Porsches are a dime a dozen and won't even get oglers at stoplights unless they say Carrera GT on the back. You may notice a difference in performance only if you regularly race on a track. On the average mountain road the Boxster is still one of the best affordable sports cars on the planet.
At some point, you've got to be satisfied with what you've got, and your car is very good at what it was designed to do. If it were me, I'd keep it, unless a really good deal came along on a 911. The Boxster was also designed, in my opinion, to put the entry point to the brand down a little and get you to move up to the next platform. I think that is working as intended as well.
The 2005 and later Boxster S is a real improvement and if you still want a roadster it is the way to go.
The 911 is a great car, but the Boxster/Cayman make better argument for fun/$. Instead of an older 911, you can get a newer Boxster S and have a better car imo, plus its a convertible and has good storage.
If you're looking to stand out, get a car with lower production numbers. An older Z8 BMW, Maser, or Aston Martin.
The perceptions of the general public really should not be a concern, most would hardly realize it's a Porsche - Most non-car-people think the M3 is something I created with a body kit, recently a kid asked me if the old Scirocco was a DeLoren ("that car out of Back to the Future"). I'm not making this up. That said Porsche people, who you *should* care what they think, generally give the 911 the highest regard, and for good reason, it's been the gold standard of Porkerly Goodness since, what 1966?
I would say you just have to take a test drive, the 911 should be available for a test drive at several dealers.
You didn't ask, but there may be advantages to waiting till you get to Fla. to purchase, it may be worth checking out what sales tax you would have to pay in each state. I'm not an expert on car financial matters of the east coast - check it out you may save considerable by buying in VA, keeping the car there for a certain amount of time, then bringing it to Fla. and not having to pay Fla. sales tax.
These cars are rust-proofed to the 9's, but offhand I'd still prefer a Florida car to a Virginia car, due to road salt concerns. No doubt most 911's are kept off salted roads but it's still something I would think about.
Actually I used to work at a Porsche dealer. The used cars we had which had the most problems were the ones which we bought from the Manheim auction in Florida. Seems like they were always higher mileage and always neglected. The PA and local cars were by far in better shape every single time.
Performance... it's a toss-up since you're comparing the 911 cabriolet, specifically. You're talking more HP, but they are a little more flexy and softer edged than their fixed roof companions where the Boxster was designed as an open-roof car from the get-go (but still improved upon by the Cayman).
If you're looking for more performance in an open roof Porsche in that price range I'd be looking at a 987 Boxster (05+). Even the base model is equal or better in performance to the early 986 S; should you step up to the the 987 S its that much better.
I would keep the Boxster. While Porsche perfected the rear-engine configuration with the 911, I like the newer design, mid-engine Boxster more. The 911 does have a higher status than the Boxster (ex. "Porsche with panties" on the Sopranos) among some, but most people won't be able even to tell the difference and most of the rest of others will like both. It won't hurt you to test the 911 and see if you like it, though.
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