I'm a bit late to the party but I'll throw my $0.10 in
$20k for a 944S2 is batE36 M3 crazy, regardless of how nice the condition is. A nice-condition tastefully-modded 951 maybe, but an S2? The Porsche market has lost it's damn mind. I love the 968 also but that particular model is a bit high as well. If you want a toy that is to be DRIVEN and not stored and polished, you shouldn't be looking at air-conditioned-garage-stored cars with perfect paint. You can get a cosmetically-4-of-5-stars car for noticeably less than a 5-star one, and it will still look nice and you will save money/have money for mods/consumables. "Investment potential" should never factor into it, especially if you truly plan on driving the car to enjoy it. And because the bubble is going to, eventually, burst.
I don't think you'll find any Elises in your price range, and a C5 Z06 will just barely make it. Both are nice, but the C5 interior is crap. Same "quality" level in the switchgear as 90s GM products, it looks like the same junk in my wife's Trailblazer and old Cavaliers. Perfect for a track weapon, not so much if it's going to be more frequently street-driven and if you want a nice regular driving experience.
You should seriously consider the S2000. AP2s are inside your price range all day long, and an AP1 in good condition is even less pricey (I'd recommend swapping to the AP2 rear subframe and upper control arms, though, better geometry) and the interior isn't too much different. It is still a great car to drive at moderate pace on the backroads. It's like a Miata on steroids. It competed directly with the 986 Boxster S, and while the base Cayman is closer in power/weight, the S2000 will be more reliable, and SIGNIFICANTLY cheaper to maintain and upgrade.
I love the E36 M3, but they are getting old at this point, and the price point for one that can track and still be nice/comfortable on the road is going to put it into a bracket where it's outclassed by newer cars. The E46 M3 is very nice, I almost bought one before I bought my STI, but as mentioned the parts prices and maintenance are German Either M3 (36 or 46) will need the rear subframe reinforcement done if you're serious about track time. Also, the SMG shouldn't be a turn-off, if you don't like it after driving it, you can convert it to regular manual for something like $1500, and that's using mostly new OEM parts.
Knurled said:
C5s are excellent cars, but they are also pretty sterile. Not as bad as 90's and newer Japanese cars, but they're still not very fun cars to drive.
What the hell are you comparing 90's Japanese cars to that you think they're "sterile"? Which ones have you driven? You realize that includes the NSX, FD3S RX-7 turbo, MkIV Supra turbo, S13 and S14 240SX, etc.? I mean, your avatar is a bridgeport, so I assume you've driven at least some of those and probably modded, but come on...