You chose the exact two vehicles that I would have recommended. Completely different in just about every way but both are fun, have a huge aftermarket support, can be purchased for relatively affordable money, and easy to work on. One for running or one for mudding, both good for a weekend toy or trip. The only negative to the Jeep is the mileage. Take your pick, you can't go wrong.
pinchvalve wrote:
I kinda feel like Maximillian getting sucked towards the black hole the Miata creates!
(kudos if you get the reference)
That movie is TERRIBLE!
Especially when you realize it came out AFTER STAR WARS and not in the 60s like I had originally thought.

Just to be different i'm going to suggest something a bit more mid engine...
pinchvalve wrote:
I think that a '72 Impala convertible would be a ton of fun, I just don't want the maintenance.
What maintenance? An out of warranty German car will require far more wrenching.
I had an epiphany on the way home...Mini is the answer.
I was following a base model with nice wheels and it occurred to me that it ticks all of the boxes.
- I want something fun to drive on the twisty roads to work every day. All Minis handle well, so I can shop any model.
- I can stop and pick up both kids, and the wife if plans change.
- I can stop at Lowes on my way home if need be for pretty chunky things.
- I can pack my huge suitcases and head to the airport.
- I can autocross it and enjoy it.
- Its essentially a BMW, so it ticks the grown-up box.
- Aftermarket support
- GRM Articles/experience
- Mini clubs
What is the reliability like? Should I go for low-mile base, or higher-mile Cooper S? What should I look for? Should I fly to Phoenix and drive one home? (Im doing that no matter what. Zero rust is a mandate)
In reply to Kenny_McCormic:
In a word: Rust. Once a car crosses the PA State Line, it starts to rust. I've seen Delorians with rusted body panels here. I've had windshield rust.
pinchvalve wrote:
I had an epiphany on the way home...Mini is the answer.
I was following a base model with nice wheels and it occurred to me that it ticks all of the boxes.
- I want something fun to drive on the twisty roads to work every day. All Minis handle well, so I can shop any model.
- I can stop and pick up both kids, and the wife if plans change.
- I can stop at Lowes on my way home if need be for pretty chunky things.
- I can pack my huge suitcases and head to the airport.
- I can autocross it and enjoy it.
- Its essentially a BMW, so it ticks the grown-up box.
- Aftermarket support
- GRM Articles/experience
- Mini clubs
What is the reliability like? Should I go for low-mile base, or higher-mile Cooper S? What should I look for? Should I fly to Phoenix and drive one home? (Im doing that no matter what. Zero rust is a mandate)
That actually is a very good choice.
mndsm
MegaDork
4/3/14 6:58 p.m.
I like your thinking. Mine is the best FWD car i've ever driven, chassis wise. I hate the berkeleying thing, but that's my problem.
I got a Skyline GTS-T for $4000 + $2000 shipping and customs fees. JDM cars are ultra-cheap. Only 68k miles (when converted from KMs)
I had earlier bought one in canada for $5700 but sold it and bought and the unmodded car above.
I like the minis. I've heard questionable reliability for certain electronics. When I worked for a Mazda dealer we used to get them all time. The non S model really surprised me with how slow it actually was. And I own a 1990 Miata. Although I didn't know it wasn't and S and half expected the power to be there.
We did have one that had to have had some suspension work done because it cornered WAY harder than the rest. Not that I drove the dealer cars like that... 
pinchvalve wrote:
- Its essentially a BMW, so it ticks the grown-up box.
All the other things are mostly true... but this one here is just lying to yourself 
Giant Purple Snorklewacker wrote:
pinchvalve wrote:
- Its essentially a BMW, so it ticks the grown-up box.
All the other things are mostly true... but this one here is just lying to yourself
Lying to myself has served me pretty well so far...
Mini's are a crapload of fun, but beware the reliability issue. Especially the S models. Some will say they've had no trouble with theirs, but there are many, many complaints and stories about major problems with them. I had an '09 S for a while and thought it was a blast to drive. All your points above are spot on for the positive things about the car. If not for the questionable reliability issue (or if I had the skills or financial resources) I'd get another one in a heartbeat.