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The Analogue Productions/Mofi etc. level of modern re-issue were worthwhile until the majors started pressing their own again and stopped licencing for the big titles. In the sense that you were getting old master tapes carefully transcribed to vinyl and pressed with a high level of craftsmanship. Speakers Corner disks are nice to handle and play too with some good titles available.
The modern Blue Note/Tone Poets can be a bit hit and miss then there's all the DOL copyright expired cheap and cheerful labels where you might as well buy a lottery ticket for the chance you will get a great copy.
The Blue Note series on CD that referenced the master copy that were produced over a long period many years ago are great too. Plenty of Japanese CD's with exquisite mastering out there but they're expensive anyway.
Personally I don't have the interest in 1 title to drop £2-£3k on a 50's jazz original but fairplay to those people who have a collection of them. No doubt they don't want to let them go for less.
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Airhead
Maybe I'm lucky/unlucky, but I never really get that difference in sound that you talk about between analogue and digital formats.
I can notice the difference in some recordings for sure - the mono 60's vinyl pressings of a bunch of Miles Davis and Thelonius Monk stuff I have is very different to the Stereo CDs I have of them; but then that's the difference between 60s mono mastering (for vinyl) vs modern stereo mastering, rather than an analogue/digital difference.
At least for older recordings, what I do like about vinyl is the sense of history when putting on a 60 year old record, which you can't get elsewhere. I don't care much for modern vinyl re-issues (unless the originals are insanely expensive) for this reason.