I do envy the fact that one can buy a lot of these cars really cheaply in America, not even have to consider a real parking budget unless they're in a very urban setting (and for only the days, if that, mostly) and that gas is cheap, insurance is cheap, etc - but in my years of driving- I've had 4 BMW's in America, an Audi, a VW, a bunch of Japanese cars - getting European cars serviced where I lived in America was a nightmare. It was to the point that if I ever live in America again, I'd probably give into better common sense and get something rated most reliable and breathe on my dice a couple times and live with not being cool.

There were foreign car specialist garages, but the reality of them was that they were mostly old VW Beetle nerds who'd invested the $200 to buy a few of the old pre-OBD and OBD1/2 override reset plugs so they could change a few filters and the oil, a new alternator, turn off the CEL's with the plug, and then charge you $1200.

Back then, it was pretty weird to roll up into a 'German car' specialist's lot and have the shiniest, nicest car amongst a bunch of dead Bugs.

In Japan, the fact that they have supernerd-level specialist shops for every car, for example strictly air-cooled 911's, or strictly Mercedes G-wagens, etc - it will feel good, like a dog finding the long last pack.

I have a small Porsche specialist with a lift a block down the street actually, next a ramen shop. Feels comforting, somehow. Wouldn't need an indie shop til I ever go off warranty, but it's cool that the cars are not ignored like they are in America, rather they are embraced as hobbies.
If you can do double parking at home for free/low cost, why not get a nice car + cheap cargo car? It's hard for me to know if that will lower your rates as it does in other countries, but it does in America, probably most places with reasonable risk assessment (though I realize Europe treats risk assessment on vehicles differently....)
I have the mentality that I want a small but nice car, and then a 'truck' if possible - I don't know what I'll be doing tomorrow, but I tend to end up doing arts and craft-y things and have a lot of junk, I make messes in order to finish my projects - I don't think I'd be able to survive with just a 911 forever. It'd be like wearing one really nice suit and shoes. Sometimes you need to wear jeans; I need that more often than renting would be convenient. It's me and her, and the dog, so they become his and her cars, eventually I think - she of course takes the nicer car....
I had an uncle (now divorced out of my family, lol) who was truly Seinfeld-esque in many facets, and he had a small 911 collection (and his brother had a similar collection of FR Porsches - 928's, 944's, etc) - and so I was able to sample my first (albeit short) seat time in a Porsche when I was pretty young and it never really wore off. He only drove one of them daily though, a basic '87 3.2 Targa - and then he always owned newer black BMW's to really drive and put miles on (effectively his wife's car) - from that alone, I did get an appreciation for a few things; apart from the real financial constraints, he always railed on how I needed to learn to drive properly before you take on a car like that - and so I did, I went to some BMWCCA schools in my old 325iS, and bought a bunch of performance driving books that were mostly from the 1980's. haha. At the time, and this was in the '90's - I'd ask him what he thought of such and such cars, and to him, the E36 M3 was scary fast at the time, when it'd just come out in the US. Crazy how times change, and the new 911 S has 400hp. I'd bet that guy is still probably driving the '87 Targa, maybe looking for a 993 to replace it, rather than any of the new ones.
I've been reading about this new 981 Boxster and Cayman that are supposed to come out, they look kind of half intriguing too. Still don't really want either of them, but a) the pocketbook would be really happy and b) they're still as much car as I need, and c) I guess I can opt of either and get a 911 variant later if I wanted. I saw some pipe-dream level photoshops on the internet of people adding 918 Spyder elements to the new Boxster, and they looked really good, but I doubt it will actually come out that way. One of my neighbors has the Boxster Spyder - seeing it enough times has made the car grow on me a tiny bit.
Buying the first year isn't the best choice for reliability, but it's better in Japan when registration and residual values are counted in - full model changes are worth $20K difference, minor changes are worth $10K in the used price, and being first year won't really factor in negatively. So waiting a few months when on the cusp of a model release is worth it.... and buying an M3 right now would not be very good financially....