1999 Porsche 911 Carrera - 46k miles - $21,500 - Portland, OR

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Examples of the most affordable 911 generation don’t come much cleaner than this striking Guards Red specimen with fewer than 50k miles.

The ad makes no mention of an IMS bearing change, likely meaning it retains the original part, a problem area for the otherwise terrific M96 engine (which made Klipnik’s list of the 10 best engines in cheap cars). Figure $2000 to get it replaced. But if you’re a gambling person, a 1999 car is actually a good bet if you want to stick with the original bearing, which came in a more robust dual-row design that year.

The $21,500 ask is perhaps a touch on the high side for a 996 without an IMS bearing upgrade, but I think it’s worth a little extra for the outstanding condition and originality.