Speaking of classic cars, I need suggestions...

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Sorry I just came upon this thread this morning. My recommendation for a car checking most of the boxes of your original post, a SAAB 900 SPG Turbo. I've owned both 900 and 9000 Turbos, great cars IMHO....performance, handling, utility, unique styling, pretty much bulletproof in my experience. Here's a link to an article on these cars for those interested. Cheers! 1985-1991 Saab 900 Turbo SPG Buyer's Guide | Hemmings
 
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Saabs are really cool cars - a friend used to own one. But when he had a mechanical issue, it was very hard to find an experienced mechanic and when he finally did, it was nearly impossible to find the required parts. He ended up selling it and thus why they were not on my list of potential car
 
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Increase your budget and...

64-67 Chevelle
66/67 Nova
87-93 5.0 Mustang notchback (tons of smog friendly bolt-on stuff here)
Grand National
Datsun 510
LS swapped XJS
My old car, miss driving this thing so much.
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I keep gravitating towards MB. I found this beauty locally - $11K asking price but I'm not sure if I want to get into the added effort of dealing with a convertible. W116 or W124 are strong contenders so far
No effort if you leave the hard top on!
 
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I would have loved to get my hands on an MG and there were a few available but they're just not practical for my current needs
They are amazingly simple by modern standards, very roomy inside for a two-seater and surprisingly tough. My first competitive rallying, as a navigator, was in an MGB and we could go full blast down the most horrible goat-tracks. For road use it was/is not quick, but if cruising along enjoying fresh air is your plan for just two people then they are fine. A couple of years ago I was talking to someone nearby with an MGBGT, the best looking MGB in my view, and I learned that a new body-in-white cost him over ten grand.

EDIT Here's an MGB story. I was driving my Mini-Cooper S waiting at a red traffic light. An MGB draws up alongside and we look at each other. Yes, that look. This was a wide road (by British standards -- Birmingham New Road) and there was a third lane at the lights. A Morris Minor takes that lane.

The lights go green. MGB and Mini-Cooper drivers drop their clutches. Both cars remain stationary with wheels spinning on the oil deposited and the Morris Minor potters gently into the distance.
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