Beats me. hag is one of a select few for whom, the content is as important as is the fidelity of the recording to me. Usually, I lean towards the well recorded aspect of music over content, save for artists such as Merle... and others of course.
Initially, the converted to disc CDs had an applette on the cover somewhere indicating that... AAD. Analog master, via analog to digital recording. Remasters were usually ADD, I believe. Much if not all today are in the DDD realm now... and consequently the fidelity is improved.
I agree, remasters aren't always better choices.
AS intent and sincere as your interest here seems to be, were I you and so disposed, I'd have a look at Merles recording lable history, and use that as your guide. Otherwise, just buy some online from half dot com, locally used, or Amazon, cheaply, and hear for yourself.
Personally, the recordings I listen to span a great range of fidelity and I always use my main rig as the template for listening... IF the quality of the recording isn't up to what I feel is acceptable, I'll play it on a lesser resolving system, which to me makes sense given the era of the orig issue... and the way some recordings were mastered for anyhow.... like 60's pop and R&B... sometimes the engineer was using a car speaker as a monitor!! or the like!! Figuring, of course, that's how the majority of their market would be playing it back