What steps forward were actually steps backward?

Sold my Mcintosh MA6900 to "upgrade" to the more "audiophile" route. It was an interesting detour but I came back to the Mcintosh and eventually upgraded to tube Mcintosh separates. Just so damn musical. I got annoyed at losing money, but the experience was educational and education is always a worthwhile expense. I learned what I like and don't like (and what's overhyped).

Another set up that I upgraded from only to be disappointed was a Pass Aleph amp and an FT Audio passive pramp. Great for the money, great anyway. Just a little short on dynamics.

Drubin, the siren call of "impressive" is paved with misery, but it is a siren call. However, having one's cake and eating it too is possible, but I believe that amount of information is, for the most part, inversely proportional to how much music survives. To put it otherwise, the more detail a system retrieves, the more difficult it is to hold the music together, bordering on impossible. The late and lamented "Listener" magazine once ran a photo of a top-of-the-line Wilson speaker with the caption "There is a use for these!" - the photo showed one being hoisted up from the water at the end of a chain on a boat: it was an anchor! We reduce the importance of timing by dubbing it "Prat," thus offhandedly dismissing it. But a system without timing is good for nothing but boat-anchors, as Listener believed. Which is why that magazine attempted to review only musical equipment, with that missing "magic" factor.

The modern inexpensive int. amp (under $1800) which I've owned recently, haven't been all that great sounding especially given their cost.(The exception, a French Kora "Explorer" which IMO is an outstanding sounding amp) The sound quality of older Mid-80's Sony "Legato" int. amps is excellent and are absolute bargins used. My 70's Kenwood KA-7100 stills sounds/performs as new. Tuners haven't advanced at all, IMO. Since my introduction (early 70's) to this crazy hobby, I've come to the conclusion that great sounding/musical systems need not cost a fortune to assemble. Much of what we've been programmed to believe is not necessarry true. I see a big demand in older equipment! Without question, hugh steps forward have been made in IC/Spk./Power cables.

Wonderful comments so far about reaching the goal of enjoying the music when we listen, rather than merely unveiling the remaining inadequacies in a system, when we upgrade part of it.
The best upgrade would be one we can audition in our own system, before we irrevocably commit our money. I have made many "upgrades" based on faith in opinion of those more experienced, until finally reaching a point where I can feel confident deciding for myself.
Home trials, with their lack of sale pressure, have proven very valuable in forming my own preferences. Joining an audio club has also been of great value, unless you already have a neighborhood circle of audio buddies.
Although it seems too obvious to state, there is musical, and audio taste, so that each of us must protect our own sense of what is really enjoyable. In every field, a guru guides the novice to reach personal sophistication, even if it is not identical to the guru's view. At least the phrase rhymes.

To Johnnatais's comments on timing, I want to comment, somewhat sheepishly because I know that what I am about to say borders on heresy or is at least un-PC in audio circles, that I wonder if the superb timing of cheaper systems (boomboxes, our car systems, clock radios) is in fact NOT preservation of the timing of music but rather a distortion of that timing.

I say this because I hear timing (and some other good things, like an extremely coherent and accessible presentation of the musical line of songs) more in these "cheap" systems than I do in live music (that's the heretical part). I've never been able to get into Springsteen songs, to take just one example, as well on my home system as I can in the car or on the clock radio, save perhaps for the songs on Nebraska. Although it was better with my old Quads than with the succession of highly-regarded dynamic speakers I've had since.

And another thing: I love detail and resolution. Why can't I have it all? :-)