Alexandre,
It is not so easy as your post suggests. Equipment performance is always limited by compromises, and unless you buy a complete DCS Vivaldi or similar (each of us should write here his favorite top digital system) you will need to make choices on the formats. And yes, I think that for 99% of the cases it will be a financial issue.
Considering the part of your post I quoted in bold - do you find any systematic correlation with the recording technique, digital original format, type of music, etc, and your preferred format, or is it a random preference? BTW, what is your current digital system?
microstrip,
I found out that the quality of a recording/pressing is intrinsic, and doesn't depend on the gear that it's played on. So, an album that sounds better on vinyl will do so no matter how good your digital is, and a badly pressed LP will always sound worse than the CD, even on an AF1 with Vertere arm.
Of course, going up the equipment ladder will ameliorate the issues with the bad/worse pressings, but they will still sound worse than other formats, IMHO.
I currently have an MSB Diamond IV with UMT Plus, as well as a Kuzma Reference + 4Point + Benz LP-S. Both are pretty solid
What is not easy is having to procure all different formats, in order to determine which one sounds best. As a rule, I buy new recordings on LP, even if it's a digital recording, and if I like it, I procure the digital (lossless) as well, either on physical CD or download. Most of the time, they're equivalent, and in some cases, the LP sounds a bit more opaque.
But I consider it part of the game. The gear are the tools I use to do all these comparisons, in order to establish which format/version I get the most pleasure from a certain recording.
To answer your question, I found out that major label reissues sound worse on CD 90% of the time, since they feel they need to "tweak" what's on the original tape, and more often than not, it sounds worse than the original. Small label releases or reissues tend to sound best in digital, since they just don't have the budget to tweak and "remaster", so they mostly do straight transfers, and when they DO have budget (like in lasercd's case), they tend to use proper guys like Bob Katz.
An example of major label stuff that, in 2014, still sounds worse in digital than analog, is Led Zeppelin. Take any crappy reissue LP, from the 80s even, and it will sounds better than the best CD, even on a Vivaldi.
alexandre