This is a fun thread. I love the self analysis as to why we do it. First and foremost to have fun. I think that I, as well as many here on this forum struggle with: if a little is good then more must be better. And that is certainly true- to a point. I have been into hifi since my college days. I always enjoyed the music but when I heard something better I was inclined to upgrade. Sometimes I might hold out for a few years but eventually I would give in. Budgeting funds for hifi was always a struggle. Since retiring I was fortunate to be able to splurge a bit on my stereo and spend what I consider way too much money for speakers, cables, dacs and amps. But the sound is amazing and I can listen to music now and not wonder what a better phono cartridge, cable, amp or speaker might sound like. In that sense, having the time to listen as well as enjoying the music without doubts is the best. I miss working sometimes but mostly I don't. I spent two full 8 hour days positioning my new speakers. Finally got them dialed in. Never would have happened, or at least not for a few years if I were still working. My brother retired and now restores wooden boats. He is talented and his boats look amazing. He enjoys doing that as I enjoy my music. I go out and play golf badly for exercise because I never took the time to improve on my golf when I was working.
I gotta talk about cars too. I lived in the Smoky Mtns for 9 years. I gotta Miata and had a lot of fun driving the twisty mountain roads on Saturdays. But of course never to sit back, I sold my fun little Miata and bought a Z4. Powerful but big and heavy. Not as fun in the mountains as I had expected. Eventually sold the Z4. Then I drove an Audi TT Roadster. What a sleeper. Every bit as fun to drive as the Miata but powerful like the Z4. The quattro makes it grip like crazy too. Still have the Audi but do not make it to the mountains much these days to really enjoy it.
As for the 911: please don't hate me for saying this. Well, it's not for me. The 911 is oh so beautiful. I get short of breath just being near one. But like too often with a beautiful woman- we just don't have much to talk about. I don't much care for driving the 911- and I lived in Stuttgart for a few years. I find it too rough and loud. I agree it's a driver's car. It has to be driven and requires full attention to the driving. Maybe I'm not really the driver I think I am. I just prefer something more refined like the Audi, or a BMW or Mercedes. Some high end Italian cars are hard to beat. I never liked the VW Beatle and the 911 is a souped up version of a Beatle. There. I said it. If you have ever driven a VW Beatle- the original rear engine air cooled Beatle you know what I am saying.