Early CDs were in some cases created without the actual master tapes. They were made from the EQ-ed LP masters (EQ-ed for vinyl play back, does not sound natural on CD) or from safety copies or 3rd or 4th gen tapes. It's only been in the last 10-15 years where record companies have gotten more careful about going into the vaults and finding the actual master tapes.
Analog to digital converters have come a long way since the time the first CDs were released. You can get a cleaner, fuller sound now from master tapes. OTOH, there's been an alarming trend in the last decade of making remastered CDs LOUDER and more compressed, stripping out dynamic range. If you compare a new "remaster" to the original CD issue, you will clearly hear (in 80-90% of cases) a much LOUDER average volume level on the new CD. Sadly most people prefer a LOUDER sound, dynamic range be damned.
Also, a chance to remaster is a chance to re-EQ. This can be both good and bad. "Mistakes" can be corrected, but many mastering engineers use the opportunity to radically alter the sound of the master tapes. You get a fatter bottom end and a sharper, brighter top end, with recessed mids. Again, average dude on the street finds that an "improvement", to hell with what the original tapes sounded like (not to mention the intention of the original artists and the engineers and producers).
So remasters are a mixed bag. Some are vast improvements, others are missed opportunities with added compression and radical re-EQ-ing. The original CDs from the 80s may be (in some cases) from inferior tape sources, and the AD conversion is primitive, but at least they aren't compressed to death and are largely un-EQ-ed (i.e. transferred "flat").
If you want to get a sense of which edition of which CD you should be looking for, I suggest hanging out at the Hoffman forums:
www.stevehoffman.tv