My buddy is looking for a used Cayman to buy, what model years would you all recommend, are they all pretty much the same, I know that there are S and non-S versions. Any model years to stay away from, thanks

Big difference between '06-'08 and '09+.

A lot depends upon your budget and what you plan to do with the car. For spirited driving on the street, any car within budget should do. If you plan to track it, the newer 97.2 (09 and later) has a better oiling system (or so they say) so the problems with the engines blowing on the track with R tires should be history.

His budget is about $35000, no track, just a fun daily to weekend driver, he is coming out of a merc sedan so should be fun for him, he is also looking at a newer Z4, I have both a Z4 and a 997TT and my advice to him was a Cayman over the Z4. Thanks for your help

at 35k, the 09 to 10 is going to be priced out of your range. since he's not tracking it, you won't have to worry about the issues with the earlier 06 to 08 models with oiling. There should be plenty of clean examples of an 06 to 07 S model that will be in that price range. good luck!