Is upgrading worth it?


I know I'm probably asking the wrong folks. I'm sure most people would upgrade their system any chance they got but at what price? I noticed the more I try to improve my system the less my music collection become listenable. Higher resolution? So much of the music I enjoyed growing up sounds more listenable on my 1970's Marantz receiver and Advent speakers so anything I do now seems like a step backwards. I need to have two systems, one for high quality audiophile approved music and a system for all the rest. Does anyone else feel this way?
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A few thoughts:

Highly produced classic rock of the 70's was engineered to sound GOOD/FUN/PLEASURABLE -- not LIVE -- through the typical home stereo system. The audiophile obsession of the '80's and later was about replicating a live acoustic experience. So, much of the gear ended up sounding etched and analytical in the quest for acoustic detail. This had the effect of snuffing the life out of the musical experience. It was depressing. Of course, the advent of digital and all of the accompanying sins of its youth, did not help matters.

I made a decision about 15 years ago that in all future upgrades, I would forego detail and resolution in the interest of tonal balance, PRaT and general musicality. This decision highly enhanced the simple enjoyment of sitting down and listening to tunes. Every subsequent upgrade has yielded greater detail, more resolution and transparency, but NOT at the expense of tonal balance and musicality.

Interestingly, I now have a system that allows me to listen and ENJOY all the old stuff from my teenage and college years. Classic rock sounds great, but so do symphonies and small jazz ensembles.
I used to feel similar - that it was necessary to have two systems: one warm system for rock and electric blues; and one revealing system for jazz, acoustic, vocals, etc. I was fortunate enough to find a gear combination which is both revealing (not THE most bloody revealing, but still very satisfying), yet retains the fullness necessary for less than stellar recorded rock (not THE best sound for rock, but satisfying enough to allow me to play nearly all of my rock collection). So it IS possible to cobble a very good system for all genre, but playback gear are always a compromise anyway. You just have to choose which attribute of sound to compromise more than the others.
For the high quality stuff I am right here in the sweet spot relishing all the details, venue ambience etc. For 50's and 60's rock I move way (open floor plan) and play while doing dishes in the other room or dancing (if no one is around) to the music. Here I concentrate on the lyrics and beat of my favorite songs rather than audiophile details. I find that this way I still enjoy my old rock stuff.
I own a 1970's receiver and found that the only music that sounds good on it is 70's music, weird. Seriously though, I can take equipment upgrades that offer higher resolution as long as it is refined, transparent, and above all musical. You can't imagine what your missing until you put together quality sounding components that have magical synergy and produce that wonderful sound that most audiophiles seek. And you don't have to get a second mortgage to accomplish this.