UPDATE: couple of my findings.
ECM: Old jazz stuff is killer however I almost fell like I shouldn't day so...perhaps this is why this didnt pop up in the forum so SSSSSHHHHHHHHHH.
Rhino: has done good with their reissues.
Sundazed: Amaing reissues. Highly recommended.
Speakers Corner: Top quality reissues. Highly recommended.
Angel: Mixed bag..some good some bad.
On Original Pressings: Lots of good advice in the thread. Listening is a plus I try to take my own headphones and even a cartridge on occaison to listen to the stuff before buying. I have become an analogue fiend, though I have little tolerance for shody old noisy vinyl. There are amazing originals, some that sound much better than their "audiophile" reissue counter parts. The only way to really tell with these is to listen.
Another key finding: Find a record shop with knowledgeable staff. By knowledgeable I mean absolutely insanely passionate about vinyl and only one degree less of an obsessive compulsive personality should do. If you are lucky enough to be in Montreal or are ever considering visiting GO TO 33 RPM (33 Aux Tours), this is arguably one of the best record stores in the world. Pete is very serious about vinyl and knows pretty much everything there is to know about vinyl and music in general. He runs a highly successful operations, I can't believe it has only been around for 5 years given the selection I would have thought they have been doing this 100 years +. I have never left there without pile of new records only to find that they are the best ones in my collection.
Montreal has a couple of other nice spots like Encore Records and Books and Beatnick.
If your ever in Toronto, "Rotate this" is the place to go.
Happy listening.