Looking to enter the Porsche family...not sure what to get.

[particlewave]

You'll get better info from a 987 forum. You might try rennlist.

[Jamesp]

Big Jake nailed it. Get the S if you want a little more performance, get as new as you can. Be aware of the IMSB issue, and buy a newer Boxster without one if it bothers you.

[Giller]

I would go with an 06 at the minimum in that age range. Beefier IMS for starters. But an 09 is the way to go if budget allows, IMO. An S is a nice upgrade, but if you've never had a Sportscar before, the base will still wow you.

[Topless]

I recently went from a 1st gen 986 to a 2009 Cayman. The 09 is a lot more car, lot more $$. You should be able to find a nice lo mi 2009 car for around $30k.