Mikey - This isn't a simple answer of which is better but I mostly disagree with all of what you said in your post (except perhaps remastering).
There are so many aspects that go into the recording process that will affect the final outcome. Before getting into those specifics, however, I generally prefer older analogue recordings that remain in the purely analogue domain from the source (musicians and instruments) and my ears and here's why.
My preference (strong preference) is that the only software that exists in the chain is that software that exists between my ears and my brain.
Any time an analogue signal is converted to the digital domain (usually multiple times nowadays), you're hearing the limitations of conversion algorithms and effectively the original sound has been lost. Not to say that it can't sound good, but now you have no ability to reach the source material as it was recorded.
Beyond that, there are so many other factors (some of those you mention) that go into the recording process that have a great effect on sound - For me, the label is often less important than the mastering artist themselves that contribute as much (when done properly) to the final recording than the artists and studio engineers themselves, let alone the equipment.
Case in point - I generally love most of the recordings that have done in Abbey Roads studios (among others) and often seek out recordings that were done there and actually keep a list of studios and mastering artists that I enjoy. Many of these were done long before the availability of digital recording capability.
Now to the topic of remastering - In general I try to avoid them particularly those that are remastered versions of artists/ albums that I already know well and enjoy - they just sound weird, compressed, unnatural, etc.
One thing that I will strongly agree on is that great equipment can't mask a bad recording - quite the contrary in that lousy gear does a better job of masking lousy recordings because on these systems, well... everything will sound lousy :)
I must say that in a perfect world I would exclusively be listening to studio master tapes on the same equipment that it was recorded and mastered on.... In fact, that might be my next obsession in the pursuit of analogue purity. There's just no denying that the fewer times the source material gets "stepped on" during the recording and production chain, the better and I vastly prefer great recordings that have never entered the digital domain - that hasn't happened in the last five years.
Greg