When you find a reissue which sounds really great, you can bet your house, the original one will be first rate, too. On the other side, when the first mastering was done average, you will have problems to find a remaster which is really top.
Bob Dylan [Freewheelin', Oh Mercy], Cat Stevens, Muddy Waters are some examples for Remaster Hype but when you go for the Original, you will be impressed, too.
When you compare, don't go for the obvious like more Bass or boosted voice, try to find out what happened with the overall - tonal - Balance, the Originals got the ok from the Artist, it was done the way he wanted it.
See MFSL Muddy Waters and the same from Classic Records. Here the MFSL is simply like a fist in your face.
Remasters make sense when the original is hard to get or super expensive, but in general it is business only. All you can do, is to ask yourself, which remaster labels really care (Classic Records, Chad Kassem, Japanese labels) and which ones do remaster without any (more or less) authentic standard compared to the original (Speakers Corner, Simply Vinyl...).
There aren't so many behind the mixing desk today who really know what to do. Most lost their jobs in the 90's (or retired) and this kind of "Art" can't be learned again. A lot of knowledge is buried now. Storage of Tapes is also a special chapter, the loss of information (mainly in the higher frequencies) is fact.
But, money makes the world go round and that's it. Each his own.