I pretty much gave up on getting new remasterings. While I think that there were a bunch of 1980s CDs that were improved by later remasterings, the results are usually subtle. I distinctly remember two famous recordings where I found a newer remastering clearly superior to a late 1980s CD issue, the Callas/De Sabata Tosca and Klemp's Brahms Requiem. I also think that some CBS CDs of their 60s recordings (before it was taken by Sony) in the late 1980s sounded quite bad, e.g. some of Casadesus/Szell Mozart. The Gould recordings sounded different as well between CBS and Sony but I am not sure which ones sounded better.Classical is mixed and mastered quite differently from rock, jazz, etc. Most notably, classical isn't nearly so low-end focused. Far fewer early digital recordings, or CD transfers of classical sounded bad. Thus didn't/don't require remaster after remaster after remaster.
I eventually also got more recent issues of some Mahler and Beethoven's Fidelio with Klemperer. I pretty much gave up, however, when I was completely unable to decide in case of some other recordings which one I preferred, one was, I think Furtwängler's Haydn #88 and Schumann #4, another might have been some Fricsay or again Klemperer/EMI because in A-B-comparison I could perceive slight differences but was totally unable to decide which one were sounding better to me.
If a recording from the stereo or digital age was pretty good in the first place and well transferred to CD there are almost no improvements to be had by further remastering, I think.