Why do I keep torturing myself with remasters?

Check some Fremer articles on Analog Planet that address this issue. He calls out labels that only do all-analog remaster/represses and some of the charlatans. 
http://www.analogplanet.com/content/reissue-labels-avoid-and-some-best-proceed-caution#gHK6bJ684z2Bo...

The best ones I'm getting these days are the 200g ones from Analogue Productions. All my Speakers Corner LPs are great too, including solo cello, large scale orchestra, Count Basie, Johnny Hartman and John Coltrane, and my ORGs are great too. 

Maybe I'm lucky or the higher number of reissues of pop and rock results in a larger number of bad ones.

I find the best sounding LP's are from the 50's/60's....RCA, DG, Capital, Mercury, etc.  

I whole heartedly agree with the above comments. I had to learn this myself in 2000 when I went back to analog in a big way - never junked my vinyl - just slowed down buying it.

All those low priced old pressings were stocking the shelves in record stores and I went for the "better" remaster.

Sorry to hear on your fire, I also have an extensive Japanese and original UK pressing vinyl collection from the late seventies so Your lost must have been huge

i buy some great reissues on jazz and very few in the pop/rock medium. They sound compressed, closed in, cymbal decay unnatural. Many have digital "enhancements". Who are these engineers putting out this crap.

you can slowly accumulate this via online - - still some giving away "batches for a few bucks" offers or go quality over quantity.  a good recording machine goes a long way

perhaps the occasional weekend trip up to Portland or down to Frisco will help fill the coffers.

there are some good remasters and you will hear about them here on SH. Be wary though, plenty of cheerleader people toting a crap sandwich release

I’ve been positively impressed by every recent MoFi reissue relative to good original pressings (Grateful Dead, Dylan, Miles Davis). Also Analog Productions(The Doors, Miles Davis mono box), and Neil Young, Peter Gabriel, and Pink Floyd archive series. The 45RPM ones can be spectacular. Other reissues have been hit or miss. SQ can be fine but is often hobbled by pressing defects(I like the Faces/Small Faces box except for one horrible white pock like acne on my favorite Ronnie Lane song.) With respect to comments above, is there a difference of opinion regarding reissues vs. remasters?

dgarretson: I think you'll be hard-pressed to make any meaningful distinctions without very specific information about the particular copies involved. A "reissue" could mean a remaster, but leaving that aside, it also includes different lacquers, pressing plants, vinyl formulations, apart from different source material -tape copies- depending on the country of origin and the country of pressing. And country of origin- band or mastering? I have records with precisely the same information in the deadwax that I know are earlier and sound better than later copies (within the same year) but that is not always the case. At the extreme, this takes you down the path of copy to copy variations, but without going that far into the weeds, is a certain lacquer number better than another even though cut at the same time- which leads to pressing plant variations. I know of no holistic way to do this on a general rule basis. There are "known" good cuts for specific rock records that are pretty easy to find with a search where there is some consensus on the sound. Otherwise, you are left with doing it yourself or relying on reviews. One last example in this vein- the early Sabbath on UK Vertigo is not only entirely different than the US pressings, but even when the same metal parts were used for later pressings when Sabbath changed labels from Vertigo to WWA, the WWAs- while bargains and "good" don't have the same immediacy as the Vertigos. On the other hand, my Neil Young "After the Gold Rush" is an RE-1. As I understand it, that's a re-cut, but it is a very early copy and usually the one I prefer. I could go on, but you get the point.....