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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Digepex brings up a major problem for a lot music audiophiles like. It can be very frustrating investing a ton of money in your system only to have a lot of your favorite music sound worse. There are brands however that can put some life and air into recordings that sound flat, lifeless and dull on many highend equipment. Just have to search that stuff out.
The trick I think to upgrading is understanding what you want or expect out of an upgrade sound wise. Balance is also important and can easily get lost in the shuffle if one focuses too much on any one element at the expense of the whole, example- soundstage or ultimate detail or dynamics. These can all exist in one system but takes a lot of careful thought and matching and not a small amount of $$$. Get comfortable with your system as it is and try replacing (or demoing) one piece or equipment change at a time to ensure you like the difference it makes without overly impacting the things you already liked. If you really dig the 70's Marantz sound, you may try a foray into the McIntosh world.
It would be very helpful if we were to know your system details, room parameters, and musical preferences.
I agree with the poster.50% of the cd's in my collection were not intended for audiophiles to sit between speakers and pick it apart. I bring this music along to hifi stores and get ridiculed for bringing it.It sounds like crap on a $20,000 system. Getting 2 systems is the solution that works for me. The nice thing about the first system for bad records is you do not have to spend alot of money for that system.