Drove a 09 Cayman S: Big mistake!

[surf40]

I think I just made a mistake. For about a year now I’ve looking over used Boxsters, probably a 2000-2004. I never really gave much thought of the difference between an S or base model. Both are way more than I have now (Civic) so I figure whatever I found would satisfy my lifelong itch. But then this last Saturday I got to drive a 2009 Cayman S (6 speed MT). I drove it on some twisty roads, and on some wide open highways. (BTW, it hits 100 mph very easy!).
So I’m wondering if an early Boxster, base or S is now going to meet my expectations? I’ve never driven any Boxster, so I don’t know what I don’t know!
I see that I can get a 2006 Cayman for about $25k here in SoCal, but then it will have the “un-replaceable” IMS bearing.
So a few scenarios are playing our in my head.

With everything thing else being equal (mileage, service record, etc), Which is better:
$35k for a 2009 Base Boxster /Cayman, or a 2007/8 Boxster/Cayman S?
Or do I stick with my original plan and get a 2000-2004 Boxster (now wanting the S!) and have money left over to sort it out?