I bifurcate cars into two clean categories, which keeps me relatively sane.
In Category 1 are the transportation appliances - these are the cars I can't/won't do any substantive work on, which get daily use. Work trucks, Mrs. Galat's daily driver, even the limo: all are OBDII ECU vehicles that never fail... right up until the point they do. I change the brakes, exhaust, batteries, and filters on these, and I do the oil changes and light routine maintenance, but if it throws a code, I take it somewhere.
I had a starting issue on the limo last month - it turned out to be a bad ground, but when I found out that the starter on a Northstar V8 is under the intake manifold, I took it into somebody. I'm just not doing it. Modern vehicles are a mess of sensors, ECUs, and plastic that breaks under a heavy hand. I once fried 3 modules on an Mercedes SLK I bought for my mom just trying to jumpstart the idiotic thing. I wanted to burn that car to the ground.
If I really need the vehicle and don't enjoy the work, I just want to swipe my card and be on my way. So that's what I do with Category 1 vehicles. It's generally possible to earn a little more money doing something I'm good at rather than something that makes me want to break things - and if it isn't, then perhaps I can't afford to own the vehicle in question. There are many such cars, most of them from the Fatherland. Guys who own and operate these cars are either better wrenches than I am, or have more disposable income, or both.
In Category 2 are vehicles I want to drive and improve for pleasure. Invariably, these are older cars and trucks and motorcycles. I can see what's happening inside with my mind's eye, and I enjoy nothing more than making something out of nothing or improving something that wasn't all that great to start with. Driving these vehicles briskly requires getting the most out of them - pushing their limits, adapting my style. I feel like I'm the master of the vehicle, rather than the other way around. This explains my speedster habit.
Modern sports cars are marvels of capability and are dead-nuts reliable. But I've not got a huge need for a car with capabilities and technology inaccessible to an ape with tools (like me). I stopped riding motorcycles when I felt like it wasn't the bike holding me back any more, it was my lack of skill. I like to improve both my mechanical skillset and my ability to drive, but owning a vehicle that's not much fun until it's going 150 mph leaves me a bit cold. A newer 911 seems like I'm along for the ride. "Driver's aids" like manuals that heel-and-toe for me, and stability controls that save my bacon if I come into a corner too hot leave me perplexed. I've said before that George Clooney would probably do a better job taking my wife on a date than I would, but I'd still rather not ride along with him while he did. There are some things I just want to do for myself, even if I do them less than perfectly. Old cars allow that.
But interesting old cars are expensive now, and are becoming static garage art. A replica is a plastic clown car, propelled by a glorified lawn mower engine designed in the 1930s by a Nazi for Adolph Hitler. I can get a new one if I wreck this one, and if I misstep on an improvement, I haven't destroyed the Mona Lisa trying to improve it.
They're perfect for a guy like me, and if I can just keep the government out of my garage, I'll happily tinker away and blast around on back roads in it for the rest of my life. Your mileage may vary, but that's why I love these cars, recognition or no.