Boxster and it's not close for me. With that budget i think you can get an '09+ and avoid IMS issues. That's about the only thing that made the early ones a maintenance concern.

Honda s2000 plus it'll hold it's value pretty well.

For $20k you could get a really nice ap2 (2nd gen, 2004-2008) example. I have an ap1 2002 and it's fun despite the lack of torque. One of the last truly mechanical cars built i.e. no fancy electronics.

Boxster also a nice choice. I'd get either of those if you're looking for something that emphasizes fun vs. overall power

Definitely find a C6 that someone else has thrown boost on already

embrace your true old man-ness

Miata. All the other cars suggested are great and fun, but the point of a convertible toy is that you park it in the extra bay of the garage, when the suns out on a lazy Sunday, you fire it up and take the scenic route to the coffee shop.

Boxters, 3 series verts, etc you do everything but the last step. Instead, you end up taking the Tesla to autozone and swapping out an o2 sensor or an alternator, etc. and wondering why you didn't just get a Miata.

KidDoc said:

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JamesPShelley said:

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Best value out there, if properly sorted. I've had mine for 2 years, and it's more fun to drive than anything ever I've owned.

eBay is a good source. However, for extraordinary specimens visit the 986 forums.

https://www.ebay.com/sch/i.html?_from=R40&_nkw=1998+boxster&_sacat=0&_sop=2

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Any idea on safety features of one this old? Hard to find info from pre 2000 models online.

Antilock brakes? Airbags side & front?

Thanks for the tip though it is a great looking year.

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Anti-lock brakes and the airbags are about the only safety features. Front and side airbags for driver and passenger. It's a car that you must be alert to drive. I purchased it for my wife... but she prefers the couch, er, Ford Edge. That thing almost drives itself and has so many bells and whistles it's maddening.

If you're handy with a wrench, that's a bonus. Small hands? Another bonus (for getting into tight spots with that wrench). I've gotten under and over the engine, and from the front side, to replace the motor mount... thermostat... water pump... oil pressure relief valve... air/oil separator... etc. Thankfully, wrenching is my hobby (thousands in tools) so I save ~$125+ an hour every time I pick up a tool.

The mid-engine placement becomes evident when you start navigating the twisties (curvy mountain roads)... it's unreal. I've blasted up the pass to my high-desert home going 100+ mph... and there was room for more. It's a fast car, but not necessarily off-the-line. Where it beats the competitors are the corners. I've learned the corner limits of my car, and it's unreal. It's like the tires are glued to the ground.

Last weekend to escape the heat wife and I drove the backside to Big Bear lake. Going home, down the mountain, it was like driving a roller coaster car... on rails. While other posters make great recommendations, you should test drive a Boxster, first generation (absent all the technology that renders the car a true analog vehicle).

Poke around on 986forum.com. There are some enthusiast cars for sale that, in my opinion, are absolute bargains.

Best wishes on your selection!