It seems like a fairly common trait of people as they age that they never regain their music enjoyment legs - that's why people splurge to buy their $1000 Bose system and never look back. Not everyone, of course, but plenty of people who seem to have memories of music deep and wide from when they were younger couldn't tell you anything about music that appeals to a younger generation currently. As time goes by and your own system continues to improve and the music collection adds another 1000 or 5000 CDs, it just opens the gap that much more
None of this is meant to be depressing - I was serious when I called it ironic. Without sounding too materialistic, I enjoy buying a dozen CDs and listening to them over the next week, or dropping a few hundred bucks on a pair of excellent seats to a U2 concert and seeing a fabulous show and not having to worry about it. I would have done it in heartbeat in my 20's if I could have, but I couldn't. Now I can. I'm not complaining. In fact, I'm enjoying the experience, just like I enjoyed the experience of having a lot more time to spend listening to music when I was younger.
The fact that I don't know many people who are really into audio and have zero close friends or relatives who would come over for an evening of listening doesn't detract from my enjoyment of audio or music, and definitely doesn't stop me from dreaming about the next upgrade. So hang onto that gear - I don't think you'll ever stop enjoying it :-) Kirk