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99 is a great year. Probably the most reliable 986 you can get.
Sure the 2.7 is faster and smoother, but the IMS becomes a genuine worry. The 2.5 is simply put, one of the best sounding motors I've ever heard short of a carb'd Ferrari. The 2.7 still sounds nice but is muted by about 50%. Factor in the shorter gearing makes the original boxster my personal favorite of the series.
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