Old vs. new

Reissue can be good only if the label sourced original master tape, most of the reissues are indeed made from a digital source. A few lables will tell us what was the source even when they are do a "180g audiophile pressing". 

So, in general it make sense to search for the original pressing when it comes to the music recorded in agalog era. Personally i alway prefer the original, buy my favorite music is fron the 70s era.

There are some vintage records recorded bad on tape or badly pressed on original vinyl, remastering and repressing in this case is a cure, but it can be analog remastering or digital remastering.  

Here is Bernie Grundman video about the subject. 

Situation can be different for people who listen to the modern music recorded originally in digital studios in the digital era. Digital recordings can be good too. 

@phillyb  I agree, you just cannot generalise.

More or less everyone agrees that CD or vinyl both fall short of the master tape, and there doesn't seem to be any easy way round this.

Of course master tapes themselves can vary in quality in many ways. 

A huge area of concern with my digital playback is that I'm unable to reproduce the dynamic performance of my vinyl rig.

I listen to classic rock on a set of Klipschorns driven by a McIntosh 275. My problem is that those old recordings were apparently recorded, produced and engineered by people under the influence of every fun chemical the late 60's/early 70's had to offer.  I swear I can hear snorting in the background of a few songs, so analog, digital, it doesn't matter when everyone involved was wasted and the mix is off.
They actually sound better on a less accurate setup, like a Kraco jamming 12 watts of digital distortion through a set of 6x9's bought at a gun show and installed in a 77 Camaro with shoe-goo.  The flowmasters give the sound a depth and extension of field that.... more chemicals please.

If you are really into LPs then contact Mike Fremer.  He knows recordings and can help you pick out the better ones from the rest.

Happy Listening.