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Welcome to the forum! You'll find lots of information here and elsewhere on the web and it is important to be informed especially if you are looking at used Boxsters.
In the used market, you set your price point and figure out what you can get. There are 3 different Boxsters (pre-2003), and it sounds like you will be looking at the first category:
97-99 Boxster with 2.5 liter engine
00-02 Boxster with 2.7 liter engine
00-02 Boxster S with 3.2 liter engine and other improvements
I don't think you'd be looking at an S unless it was unusually high mileage or some other factor--better to get a more pristine 2.5 liter Boxster because of maintenance concerns.
Sounds like you want to purchase in the fall/winter? Perfect for buying a convertible; you'll get your best deals at this time!
-Charlie
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