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I think after I finally get my 991 I'm gonna have to look into getting an older one too...
If you are a dedicated tinkerer with reasonable mechanical aptitude and don't mind skinned knuckles and oil stains, or have a good mechanic that you don't mind being very friendly with often, an early 911 also provides other sorts of fun that new cars don't. Its guts are reasonably accessible and it has lots of dynamic quirks that can be resolved or mastered. It keeps you involved all the time- not just when driving!