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?
"Does anyone else feel this way?"

I don't. What are the upgrades you're referring to?
It's true, better, lower distortion systems expose the quality of the recording, good and bad. My solution for the bad? Listen at lower levels and use the tone controls, or play the bad recordings as background music.
Upgrades should be done so your collection is more listenable than with 1970 Marantz receiver.
"high quality audiophile approved music "

For once I am speechless.
Choose upgrades that make your music more enjoyable to you, not less. It can be done.
Odd. If you like the 1970 Marantz receiver sound.. Why bother to upgrade?
I find i love the increased clarity my nwer additions have given me, for all recordings...
I accept the limitations of old recordings..
In fact i am again listening to 1940's Jazz... Wonderful, limitations and all.
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.
Digepix. I know exactly what you are talking back. Its not that you like the sound of you old amp better, it's just more forgiving on lesser recordings. Very common problem. A lot of people make that mistake: they run around with a bunch of audiophile CD's to test and set up the equipment and when they listen to what they really like, they realize a mistake was made. I can give 2 suggestions. 1. Since you still have your old system, keep it and just use it for certain problem recordings. 2. Get an eq. Run a straight cable from your CD player to the preamp and another one from the CD player to the eq. Then take another IC and go from the eq to a different input on your preamp. That way you can switch back and forth.
It's true that a more revealing system will reveal more flaws. But it'll also reveal more strengths in a poor recording too. If all you're focusing on is the flaws, that's all you'll hear.

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

My system isn't known for being warm, smooth, forgiving, etc. (Bryston B60, Audio Physic Yara Evolution bookshelves, Rega DAC (not as forgiving as people think)). I've also heard my music on $100k systems, and bad recordings are still bad, yet they're still highly enjoyable. My library consists of rock, classic rock, metal, and alternative almost exclusively. With the exception of Pink Floyd and one or two others, none of this stuff would be 'audiophile approved.'

There are very, very few albums I can't listen through my stereo due to sonics. Metallica's Death Magnetic being one. About 3 or 4 tracks into it, the amount of compression rely wears me down. I can't listen to it much further on my iPod either, so it's not like my system is to blame. The only place I can listen to it is in my car.
"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.

If you're continually upgrading and become less satisfied with the result you need to be "A" doing more research and"B"auditioning,providing of course you are residing in an urban environment.
you could not be MORE CORRECT regarding a LOT of music from past recordings/groups, ESPECIALLY rock albums, but many others as well. some time ago (1970's) i had a Fisher receiver, Fisher speakers, and a Garrard turntable.
the entire system set me back $350 (all the wire was included).
whether it was Gentle Giant, The Who, Simon and Garfunkel, etc. EVERYTHING sounded great. later i upgraded to a Thorens which was a far more elegant machine, but truthfully the Garrard worked fine even with all of the cheap plastic parts.
everything was fine even a couple of changes more down the road, UNTIL-
My "GREAT DOWNFALL" - THIS began with the purchase of B&W 801 speakers. now my classic-rock collection started to sound like the music was pieced together with spit and glue- tonal variations, pauses and timing errors in the mixing process, too much of this and too little of that, etc. started to make me gravitate to classical recordings, blue-note jazz, acoustic folk groups, female vocals, etc. Cream and C,S,N &Y didn't sound so good anymore. my beloved J.Taylor alblum (S.B. James) sounded constricted and artificial.
Anyway, I feel there is a good reason to advance to a certain level of Speaker Resolution and then hold off- AT LEAST until you understand what is certainly going to happen to your ability to relax and enjoy "those recordings i have alluded to". when you get a pair of super-speakers with kevlar, carbon fiber, beryllium, diamonds, and dense HEAVY cabinets, ELLA will send you into rapture, the NY Philharmonic will invite you INTO Lincoln Center for a concert,
T.Monk will save you a seat in a downtown club. but don't expect a sloppy production to sound good as well.
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.
Bravo Turboglo.... my thoughts exactly.
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.
I agree with all those who propose a second system for older recorded music. To me, listening to music often includes a nostalgic factor that brings more of the good memories when the music sounds as it was then.

But when it comes to modern recordings, considering the amount of info they carry and the sounding performance they can throw in terms of dynamics and soundstaging, a top notch sounding equipment is the priority to me.
70s music sounds fine on my system. I like to use bad recordings to test my gear- it should not editorialize if the recording is messed up. I have found that a lot of equipment *will* get upset when you play a bad recording, and make it worse, even though the same equipment will play good recordings OK.

However I don't think of 70s recordings as being particularly bad, although some are lacking bass and are over-produced. But that's been an on-going problem.

I listen to rock, folk, classical, jazz; whatever appeals. The decade IMO has nothing to do with it being a good or bad recording, although I don't like the increase in digtaliss that occurred in the later decades.

Overall, the more I have improved my system, the better all of my recordings have become. My collection is about 6000 LPs right now...
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).
Its way cool spend cash!!
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.