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

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!

georgehifi has brought up one of the factors to consider. George is a dynamic range true believer. He always likes the release with the greatest dynamic range. There is nothing wrong with that.

Dynamic range is the difference between the loudest and quietest sounds on a song or track. In the 90s and continuing to this day, record companies began compressing music. You may have heard of the Loudness Wars. This is what they are talking about. Albums with too low a dynamic range sound loud and harsh. They will give you a headache or make you want to turn the volume down.

Greater dynamic range is always desirable but, IMHO, sometimes an album with lower dynamic range (but not too low a dynamic range) can sound better due to greater clarity, better mix, etc. It’s one factor to be aware of and you should try to find out by comparing different releases of the same album with different dynamic ranges what level of dynamic range you are comfortable with.

I also wanted to add that you don’t always need to find the best release of an album. People disagree about which is the best and the best may be expensive and hard to find. The second or third best might be good enough and the difference between them and the best may not be as great as the impression you get by reading the SH forums. There are people there that are sound quality extremists. Most people would never notice some of the sound problems they find intolerable.

Again, Good Luck!

optimize, I almost included the road noise point in my post, but felt I had gone on long enough. You’re right, the car is a good place for lower dynamic range recordings. I don’t think the OP wants to upgrade his album collection for use in his car though.

While I'm at it, let me recommend getting a streamer and DAC and a subscription to Qobuz or Tidal, as an alternative to replacing your album collection.  Both have a free one month trial period.  Qobuz has a large number of hi-res recordings and Tidal has a fair number of MQA recordings.  You can listen to a lot of hi-res music for $15 to $20 a month and when you decide which albums you really want a physical copy of you can seek out the best version of those.  It might save you some time and trouble.