Your interpretation of the Blue Notes as bright and less natural than Contemporary (Label I presume?)is interesting. There's a big difference between BNs on vinyl and on CD. They are bright on CD. In fact I once panned Rudy Van Gelder based on the quality of the cds. RVG BN's are not perfect by any means. Pianos typically sound terrible. But on good pressings the horns and drums usually sound wonderful. Then there's a whole other debate about whether stereo or mono recordings are better (I prefer mono).
Contemporary made some great recordings too. They were also an early adopter of Stereo and some of these are excellent. Their pianos sound pretty good for the day. See if you can find Shelly Manne and his Men Play Peter Gunn (Contemporary Stereo (S)7025). Columbias in general are very inexpensive. Columbia was the biggest label around. They'd let smaller labels develop talent, then they'd come in, offer big money and take the best artists. Miles Davis from Prestige, Monk from Riverside, Brubeck from Fantasy, Ray Charles from Atlantic. As a consequence they printed a ton of records so they're cheap. On BLue Note, by comparison, there are some records that only got about 500 original pressings.
My Horace Silver record is a modern reissue. I think its a 200G reissue that I got from Acoustic Sounds.
Your 'Songs for My Father' are both reissues. The original - I believe - would have been blue and white with "New York, New York" on the label and most like the RVG stamp in the dead wax.
Chronologically the labels on 33 RPM vinyl would go (roughly) Lexington Ave (mid-late 50s); West 63rd St (Late 50's to early 60s); New York, New York (Early to mid 60's); Division of Liberty (Late 60s) and then sometime later they went to United Artists and the blue labels but I'm not sure when.
They way I look at it is this: If I'm contemplating buying an original and it costs more that about $25, I'll check and see if a high quality new reissue is available. If it is I'll go with the reissue every time.