It’s a tough choice for me.
My first thought is a 1957 Chevy Bel-Air. Classic great-looking Detroit iron, with a Chevy small-block V8. That engine was introduced in 1955, and by 1957, they had worked out the kinks.
But then I thought about a 1968 Austin Mini Cooper. I’ve driven one (that would have been about 1974, certainly not recently), and what a blast it was to drive! Great for getting around town, easy on gas, and did I mention what a blast it was to drive? 
Yeah, the only trouble with those was that the grill was metal and would get dinged up over time and have to be beaten out or replaced. Also people would steal the hood ornament if it was left outside.
1976 Porsche 911 Targa. I’m not a fan of Targas, as I prefer coupés. I prefer the fender flares of the 911SC (and Carrera), and the '76 911s had ‘something’ wrong with their engines (timing chain?) that makes them a little suspect. But my 911SC was the most fun car I’ve ever owned. I would enjoy a '76. And if I don’t have the flares, then I may as well go for the Targa.
I’ve never driven a 69, but a friend of mine had a 67 RS/SS. Even with just a 350 that we had worked over, that car was a beast. 140 mph or so in no time. It handled well, but if you broke the back end loose, you’d better have it pointed where you wanted the car to go when it grabbed again.
Thought about buying an old Cooper more than once. The only thing that really kept me from it is that I couldn’t imagine driving one on the freeway in the US.
Good point, and I thought about that. But though my city has a couple of expressways, they would never be mistaken for a freeway. I’m thinking more of the Mini as an urban daily driver, shuttling me around my little city, in which I can get from one side of town to the other in 15 to 20 minutes, depending on whether I get the lights. The Mini would be perfect for that.
I’d still like one. I figure that if I need to take the freeway for destinations a few hours (or more) away, I could rent something a bigger and more modern.
Friend of mine had an Austin–Healey Sprite. She said it was a real babe magnet, but apparently it spent more time in the shop than on the road?
IIRC, the ‘76 911 engines’ biggest weakness was the magnesium cases. They were prone to leaking and the studs pulling. That being said, earlier 911 models drive so differently from SCs, and even more differently than mid-'80s Carreras. There’s a lightness to them that’s just so fun to flick them around corners. I just wouldn’t want to be the one holding the pink slip when it came time to rebuild the engine!
That’d be my top choice, too. Probably a '69 or '70 Mach 1:
My runners-up would be a 1970 Plymouth Superbird (just because it’s kind of ridiculously awesome):
…an early 1970s Porsche 911:
…and a 1957 Chevrolet Nomad:
Daily driver?
Are we allowed to supplement it with a “special use” car (i.e - My current daily driver is a Mazda Demio / Mazda 1) but it is supplmented with a Ford Territory for towing / travelling etc
If it’s got to be a single car
Maybe a series 1 Range Rover
Or a Leyland P76 Wagon
Jensen Interceptor for the cool factor (but the running costs would be killer)
Or a Triumph 2500 Estate
Also remembering that it would need to be a right hand drive
If we could ignore that part …some reconsideration might be required
How about depreciaton or what happens if I have a parking whoopsie?
Do I need to take into consideration possibility of damaging it and repairs?
1963 VW Deluxe Transporter
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Just a simple station wagon for me.
A 1973 Chevelle Malibu SS Station Wagon 454.
Very nice. A limited-run muscle car station wagon. 
Ooooooooo, the flip out windshield!
Hehe, I had a customer with a 70-72 Oldsmobile Vista Cruiser with a Rocket 455 in it. It wouldn’t beat my Ranchero with a hopped up 351 in it, but it moved quite nicely.
1969 Pontiac GTO The Judge
Is that the same as the “Dukes of Hazard” car? (really asking…kinda looks like it)
No.
The Dukes drove a 1969 Dodge Charger.
Very nice! I seem to recall Rick Harrison on “Pawn Stars” remarking that VW microbuses with the roof windows above the regular windows were worth a lot more than later models without.
Now, the real question: would you paint it chartreuse and put sixteen long-haired Friends of Jesus in it?
A 1967 Rolls Royce Silver Shadow – one of the most elegant car designs every produced. The previous generation was pretty cool, too, but looking quite dated by now. The new ones are positively ugly, IMHO.
My second choice (yes, I’m weird) would be an MCI highway bus. Man, one of those beauties would make a great camper – or even a mobile home! (I’d have to upgrade my license with an air brake endorsement.)
All the cars from that era were terrible. Terrible brakes, terrible steering, crossply tyres, and they practically rusted out on the dealer’s lot.
Hey, why not? An air brake endorsement is easy; all you need to know is that Westinghouse safety brakes (air brakes) are the opposite of hydraulic brakes, and you should be golden. PM me if you want more info.
Why yes, I did once own a CDL, with an air brake endorsement. I gave up my CDL once it became apparent that I’d no longer be driving truck. Back to a regular driver’s license for me, though in a jam, I’d suggest that I can get your semi out of it. Still remember my temps, pressures, shift patterns, etc.
A highway bus? No problem.