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The Porsche used car mantra is "Buy the newest car you can afford". All the 996's had rear main seal issues of varying degrees from a small leak to total failure. D-chunking of the engine, where a "D" shaped hunk of the lower cylinder shoulder cracks off and winds up in the engine was also an issue in many of the early cars, '98-'99, which was corrected on the '00 and beyond engines. Coolant tank cracks on the pre -'03 cars and poor sealing of the coolant tank caps is still an issue with even the 2008 models due to poor design in my opinion.
I would strongly suggest you have a pre-purchase inspection (PPI) done by a pro who knows Porsches and knows what to look for. You'll want a clean bill of health before you buy and as there are plenty of these cars available you can be particular about which car you buy. As for me, I owned a 2001 Boxster, purchased new, drove it 7 years and had no major issues with it. Traded it in on a '07 C4S, also purchased, new and have been very happy with it. I love these cars warts and all.
Doing your homework before you buy can save you lots of $$'s and big headaches in the long run. Good luck with your search.
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