Is upgrading worth it?

"I bought a system to listen to my music on. I don't buy music to listen to my system. There's a difference."

Well Said!!

I've never had the money to indulge my whims. Or the inclination to skip other stuff to go with upgrade fever.
So, my system remains stable for long time periods. Before the upgrade I did from 3 to 5 years ago, my system had been stable for about 2 decades. Stuff just wore out. I'd like to get my original 14 bit Magnevox CD player fixed.

I've got a few CDs which simply don't sound right....and in those cases, not even in the car.

I think some with upgrade fever get caught up in trying to hit a moving target.

There are mistakes a lot of people make during upgrades. When you buy something new, and it has a sonic characteristic that is really not liked, pass it on. Everything I bought new or used, if I didn't like it at first, I let it go. When I get something new and like it right out of the box, I know it's a keeper.

A lot of people get caught thinking it will improve with break-in. Then, they start getting accustomed to that sound that they didn't like. I do the opposite. It needs to make me happy right at the beginning. Then, if there are any changes, it seems to be for the better, after it builds up some hours. Result, I'm happy with everything in my system.

If you make a compromise with these new components, and worse yet several of them, that same characteristic you didn't like in the beginning can still be there, maybe not as much of it, but still there. If that happened with a lot of you components, it adds up more, and you probably have a whole system you don't like.

Keep the new items you enjoy out of the box. Then you may be really happy with the end result, especially if most of it turned out better (after hours were put on it) like I am.
I think this mistake is made too often. It takes more trial and error. But, in the end it's worth it, at least for me.

I'll admit that there are plenty of recordings out there that sound like crap on a high-resolution system. But the really good recordings sound wonderful too. You have to decide where you fall in the "true to the source material" camp.

In addition to what's been mentioned above, it's important to keep your system balanced from a resolution perspective. It's possible that some of what you're hearing is new components revealing weaknesses in older components, e.g., new preamp revealing problems with a source component or new speakers revealing problems with the preamp, amp or source.

As is also mentioned above it's possible to upgrade a system without making almost everything totally unlistenable. To do this you have to first identify the characteristics about the sound of your current system that are important TO YOU. Then, when upgrading, research the prospective components to determine if they have those characteristics. If you can't listen to prospective components in your system before you buy, then this process will carry the risk of being trial and error to some extent.

I expect the music of an era gets recorded with an eye towards the equipment of an era, which might account for the "vintage effect" described in the OP. I remember being shocked at how "right" Dylan's "Desire" sounded on some old speakers from the 70s, with their huge sloppy woofers.

That said, music played audiophile gear needn't sound like edgy etchings from hell, though it certainly can.

John