Music from ripped CDs (server)

Currently using oppo MOD CD player.  If I download my CDs to a music server (think I can still use oppo mod as D/A) would the sound be significantly worse?  (Robert Harley said it can be better, but I'm skeptical)

Suggestions for music servers under about $3k?

Do the servers have user interfaces that are well written so I can find what I want easily and  e.g. if I have several performances of a Beethoven symphony I can find the one I want easily?

Thanks.