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Rising Star
Around here those models are a dime a dozen.
Probably an unpopular opinion, but I'd rather get a C3 Vette and do a light restomod.
This is a unique one. Never sold in the US.
https://bringatrailer.com/listing/1998-bmw-323ti-2/
Late 60's Chevy Chevelle
I’d stick to the E46. E36 parts are getting harder to find.
I have owned multiple E36 and E46, there is no such thing as an E40.
90s and early 2000s BMWs are excellent cars, but are old at this point and finding good ones is tough. Rust is a problem on both the E36 and E46, and rear subframe tears are common on the E46 and is best addressed by reinforcing prior to failure.
Engines and transmissions are generally strong, but the S54 (E46 M3) has had some issues with rod bearings and the optional SMG transmission is costly to fix.
The E46 has a far nicer interior - E36 interior parts have gotten brittle, door cards delaminate, and certain parts are no longer available to keep it looking nice.
In either case, buy the nicest one you can get afford and read up on that particular model’s quirks - if you can’t do 95% of the maintenance yourself, you may regret buying one. If you can handle most of the repairs, then have fun - they’re great cars and relatively easy to work on.
E39 M5 if you can find one (high miles) or a 540 with the manual (if you can find one). Another option are old AMGs that aren’t modded to heck. Think a high mileage e55 or s55.
E46 is my favorite body style of bmw. I miss mine!
Miata or Boxster
At that price point, I'd probably build a C6 or C7 corvette.
You can buy pretty nice Mercedes 280 SEL 4.5s in this range. That would be my pick.
OP, knowing your goals would make a suggestion more relevant (weekend cruiser, backroad carver, hpde/track car, general restoration, etc)
LS swap Miata. Can start slow and build it however you see fit.