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.
berner99
Hi Berner,  I have replaced many, probably most, of my CDs purchased 20-30 years ago with reissues that are described as remasters. Most are much better than the originals.  The Moody Blues classic seven albums have been reissued several times.  The last set I purchased was a project overseen by Justin Hayward. I like them more than my MFSL gold set.  Traffic's "Low Spark" and "Shootout at the Fantasy Factory" have been reissued with improvement heard.  Look for your favorites, and you will find most have been offered again as remasters that are well worth the price.  
Yes it does matter. There are good and bad sounding 80s cds, remasters and hi-res versions of most of the albums you're looking for.  There are quite a few pressings of most popular albums and there is no simple rule to determine which is best.  Sometimes it's the original cd, sometimes a remaster, sometimes a Japanese or German import and sometimes an audiophile pressing.

The best sounding version of a particular album is a frequent topic on the Steve Hoffman Music Forums.  You'll just have to go there and search the forum for a discussion of the album you're interested in.  There's no simple way to do that either.  

When you determine the particular release you want, you can look for it on Discogs where albums are supposed to be listed for sale by specific release (but the listings aren't always correct so you may want to ask the seller to check before you buy).  The Hoffman forums also have a classified section where you can pick up some of the releases determined to be the best.

Good Luck!
Players over the last 10 years are SOOO much better sounding than they were for a very long time. In particular, redbook playback is much better.

MFSL - Really variable. Have a really bad Pink Floyed DSotM. You are better off with older releases.