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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To my ears settling for an ancient cheap system for 50s, 60s, 70s music is absurd. It takes some work, but you can get amazing results that can magically turn old distorted CDs into gold without equalization or other evil tools.
Supremes, Motown, Phil Spector Wall of Sound girl groups, 80's Rock-of-Ages music, progressive rock... it's all good with a little effort and a good ear.
My main suggestion is to put some tubes in the chain (at least in the preamp only, like I do).
I don't always care about new features. I am fine with older equipment. I use to watch a lot of movies in surround sound, but mainly listen to cds and online radio more. I don't think upgrading is always worth it. If it's a certain model that you really want go for it. so many new electronics have a high failure rate anymore. Check out each models reviews that you want a lot. Doing this saved me thousands in bad receivers that I would have bought.