I have used frankly awful equipment in the past (especially when I was younger) and there is no way I want to return to those days. I'm not obsessive about it (my left and right speaker are wired using different types of wire, for instance - oh, the blasphemy!) but to my ears what I have sounds good (Marantz PM-48 amp, Marantz CD-63mkII CD player, Marantz graphic equaliser thingybob whose model number evades me, Mission 730 speakers), and I wouldn't want something that sounds less smooth, less "spacious" or basically just plain good than what I have currently.
You can't have moments like chuckling with your other half about the stereo separation while listening to "Unsquare Dance" by the Dave Brubeck Quartet on a crappy little speaker dock thing.