All this is reminiscent of the "discussions" (read: arguments) still raging about the merits of vacuum tubes vs. I.C.'s. Many audiophiles claim that in order to hear music at it's best one should play L.P's (probably stored in a pyramid when not in use to keep them pure) using a valve amp. with oxygen free cables (I STILL have a problem with this one ) and gold connectors.
Only analogue signals, of course, none of this digital crap!

As to whether analogue is better than digital, unless you're listening to your music in an anechoic chamber, using carefully selected components (read: lots of money), and you have very good hearing, I seriously doubt you will notice the difference. Bear in mind, also, that if you've been exposed to high levels of noise while growing up (e.g. concerts, nightclubs, playing so-called modern music very loud), then the chances are very high that your hearing has deteriorated anyhow.

At the end of the day, it is largely subjective - if you're happy with what you're recording (and playing) then that's really all that matters. Use good source material, not MP3, copy as CDDA/wave and enjoy.

P.S. if you're playing it back through small PC-type speakers, then anything, no matter what, is going to sound crappy regardless