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I'd say tell him to go for the 996. Look enough and you will find a well taken care of one for the mid 20's, low 30's if he likes the look/drive of the 4S and wants to stretch a bit. Most maintained ones will have the LN IMS fix to take that worry off the table and if not just budget $2500-$3000 and do that and the clutch at the same time. I was a big 'no-996's' guy for years and ended up selling my 997C4S to get into a 996 40ThAE which I find much more enjoyable to drive. The 996 is at or near the rock bottom of its depreciation curve and provides all the Porsche driving experience for half the price of similar 997's.
Just my opinion. YMMV
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