CD sound quality: original pressings vs regular remaster vs MFSL, etc

I'm expanding my music collections and acquiring/reacquiring many very old works e,g, Cat Stevens, Traffic, Moody Blues, Coltrane/Miles Davis/Brubeck, and some classical and newer popular works as well.

Does it matter much whether the disk I get is "original" older pressing, or a remastered version?  Or a MFSL?

I remember CDs were unlistenable first 5-10 years, but no idea if that was the disk or the players and not sure I'd run across any used CDs that old anyway.

Thanks for your time.