better gear, worse recordings

As an example of what you're talking about, the late 60s/early 70s and beyond DG and CBS Masterworks recordings and the old RCA Dynagrooves stand out to me. The two former were heavily multi-miked recordings using very hot treble mixes and poor bass, mixed to sound like what the engineer wanted to hear (hence the 20 foot wide piano soloist or larger than life violinist that Sugarbrie so aptly points out) rather than what the orchestra played, which could sound good on inexpensive record players but did not fare well when you got them on a system which could realistically play back what was on the disc. The Dynagrooves were intentionally and heavily equalized by RCA to make up for the deficiencies of the record players of the time; Gordon Holt, I remember, was absolutely incensed about this, particularly considering the great recordings RCA had done in the past. While a noble idea, perhaps, they do not come close to the sound RCA had with its earlier efforts when played on high end or even modest modern turntables. And all those 60s rock records of my youth, of course, were mixed to sound good on a 3-inch transistor radio so that I would buy them (which, of course, as the ultimate consumer I did), so it's a miracle they are listenable at all on a good system (although many of them, particularly the Motown stuff, come across surprisingly well). On the other hand, the Vox and Vanguard records, which in my experience sounded mediocre due to the less than stellar vinyl they were pressed on (I may have heard poor pressings, I admit), are sonic eye-openers on both SACD and the vinyl reissues that have come out. So you're right, it does work both ways. I have tried to gear my system to be accurate but to err on the side of musicality, so that I can enjoy great performances that aren't pristinely recorded. The good news with recent classical recordings is that, in general, they seem to be better recorded on the whole now than they were, say, 20 years ago, when multi-miking seemed to be the rage. Good thread, looking forward to seeing other posts.