Why do I keep torturing myself with remasters?

I had left about 15 boxes of my LPs in my parents basement when I moved out. After 10 years of a lot of moving around the country, I finally settled down. I went to my parents to pickup my LPs only to find my kid brother had sold them at one of my parent's garage sales for 10 cents an LP!?

I had been collecting LPs since the late 60's (lots of jazz, big band and rock) and they were mostly first issues. Man, I was pissed!

It's been a slow (and expensive) process re-establishing my collection. Nowadays, with my current digital rig (Esoteric DV-50S or pc feeding into a Teac UD-501), I'll only buy the LP if:

a). the digital recording is complete shiite, or
b). it's only available on LP.

But, like 'hi-res' files, I've become wary of the marketing of re-mastered LPs. Not all remastered LPs are sonically superior to the original.

Although, admittedly, finding decent copies of LPs pressed in the 50's is becoming really difficult.

While the quality of some (most?) of the early digital recordings were limited by the equipment available at the time, it is very easy now for a modern digital (DSD) recording to match (or, in some cases, exceed) vinyl in terms of frequency response. Admittedly, this has no bearing on whether or not you prefer the sound of vinyl over digital. The fidelity of one's playback system exerts a large influence in this as well.

But recordings stored on analog tape are subject to degradation due to how the recording was made in the first place (i.e. magnetism). The longer an analog tape is stored, the more 'bleed through' of the signal to adjacent parts of the tape you get (unless you take proactive measures from the beginning).

Alan Shaw (of Harbeth speakers in the UK) did interesting experiment. Here's a link to it: http://www.harbeth.co.uk/usergroup/showthread.php?1477-Early-analogue-recordings-amp-an-evaluation-of-analogue-technology. He analyzed 30 year old tape recordings spectrally and found instances of pre and post echoes in quiet parts of the tape (i.e. where you'd normally expect silence). This was unnoticeable in the busier passages but it was still there.

So remastered recordings that use the original master analog tape will have some unwanted signal introduced into the new recording. Removing it can contribute to a degradation of the original recording. 

Direct-to-disk recordings would obviously not have to deal with this issue.