I feel like I've been in the same boat as you. I recently upgraded equipment and I'm getting back into vinyl purchasing mode. A few years ago I went through most of the issues you're going through. I never made it up to paying for pristine original blue notes or others, but I have a few decent early pressings so I have a good idea of what I'm missing. I have several with surface noise on my ZYX Airy, which is very iritating. FWIW, here are some comments:
These suggestions assume you like the 1950s-60s Blue Note music the best, along with other good stuff from labels such as New Jazz, Prestige, Vee Jay, etc...
1. These comments assume your budget is no more than $50 per LP (and preferrable much cheaper), so if I say something sounds good, it is relative to what is generally available in that price range (either used or new reissue). If price were no object, I would go for near mint first pressings. I haven't compared near mint first pressings to the reissues or later pressings, so I don't know whether they are worth the extra money. Maybe someone else can chime in on this point.
2. By far the best value are the OJC's. They were analog recordings and the vinyl is very quiet on almost all the ones I own. When you can find them, they are cheap used ($5-$10) and many are still available new. For more money, the Analogue Productions 45RPM's are available for many recordings (I have a few and they sound great, and for what they are, they are a great value) and Analogue Productions 180g versions of the same OJC recordings also sound very good.
3. For Blue Notes, as you noted, the Japanese King and Liberty pressings are a good deal if you can find clean copies for good prices. I have some of the new series of Classic Records reissues, and I think they sound good compared to the King or Liberty, especially when you factor in the potential for surface noise on less than mint King or Liberty copies. Before Classic came out with its new series, I focused primarily on Mosaic sets, since it was the easiest way to acquire quiet Blue Notes. The vinyl is quiet and the recordings are good. You have the alternative takes, which you may not like, but the Mosaics are comprehensive and often include tracks from very rare or otherwise unattainable LP's. I also have some of the Mosaic CD sets, which are uniformly excellent. The nice thing about Mosaic vinyl sets is that every used set I've purchased (even an ex-library box) has had pretty much zero surface noise.
4. Now, here's something else that you may have figured out. There are going to be several must have LP's that you really want, such as the great Paul Chambers stuff, but you're going to have a hard time finding any acceptable versions in vinyl for the $50 per LP budget. This is where I shifted to CD's. Generally, the Japanese mini-LP sleeve versions of the Blue Note recordings are much nicer than the RVG US CD's. If you look around, you can get them directly from Japan for about $25 per CD.
5. If you're into Paul Chambers, I recommend the Mosaic Complete Vee Jay Paul Chambers-Wynton Kelly Sessions CD Box Set. The Mosaic Select Paul Chambers CD Box (still available new) is a good value if you don't have the Paul Chambers Japanese mini-LP CD's.
6. If you don't have a copy, order Doug Watkins - Watkins At Large (Classic). I have the King pressing, which sounds great, and I've ordered a copy of the Classic reissue to compare, since it is one of my favorite jazz LP's.
7. Although Speakers Corner doesn't have much Jazz, if you like any of the jazz in their catalog, the reissues are excellent. If you don't have it, I'd highly recommend Mingus, Mingus, Mingus from Speakers Corner. There are others that are excellent, but that is the first record that comes to mind.
Hope you find this helpful.