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

[apswater]

In my opinion, you should look for the one with the lowest mileage you can afford. As S is better than a base but a base is still very enjoyable. The IMS bearing thing is very over stated but when you change the clutch, upgrade the bearing. I recently picked up a 2000 S with 12,000 miles for a great price. You never know what you are going to find. Just keep looking for ultra low miles and dont worry about the year so much.