If price doesn't matter -- go with the newer car. Consider getting a 100K mile CPO warranty too if possible.
There is a very big change between the 986 model (last year was '04) and the 987 model that started in '05. So the car is two years newer & its the newer platform. That justifies the price delta.
Now, regarding three owners -- something to think about is a Boxster is a love-it or hate-it car. Some folks love it, then regret it. Sometimes lifestyles change. Sometimes they decide to "upgrade" to a 911 or a Cayman (or who knows). I wouldn't over think the 3 owner thing with a Boxster. I suspect its not that unusal.
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SOLD - 2002 Boxster S - PSM, Litronics, De-ambered, Bird Bike Rack, Hardtop, RMS leak...
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