Ole- for some of those uber collectible records, that’s where a good remaster would pay off. One of the reasons why some of these records fetch big money now is that the record at the time of release wasn’t popular and few copies were pressed. (Or there could be a host of other reasons, contractual dispute with label, failure to promote at the time, etc. but the result, whatever the reason, is there are few extant copies). Once a record like that has been identified by collectors or listeners as something special, the price skyrockets. However, they remain niche products that wouldn’t justify the investment in tracking down the tapes (assuming they exist), licensing the master and artwork, hiring a good mastering engineer and bearing the costs of manufacture and distribution. Selling even a thousand copies might be a struggle.
With some exceptions, the better reissue houses tend to stick with less risky reissues and you are left with the original at crazy prices (and even at that, sometimes hard to find without problems) or shoddy re-do’s from questionable sources. Sometimes, you can get lucky- you will hear of "barn finds" (really a vintage car term but same deal with records) of a 3 or 4 or 5 figure record that someone found in a bin for almost nothing, but in my experience, that’s not really very common....
I didn’t get into UK Vertigo Swirls until a few years ago and by then, they were already nutty money (and not just the Black Sabbaths which are some of the most common Swirls, b/c those actually sold the most). Ditto, some of the more obscure Italian or German prog stuff. Just wasn’t on my radar in the mid-’70s.