@grislybutter - I don't want to sidetrack this discussion with the MoFi situation but there are bad sounding all analog records and good sounding records that used digital processes. I have a thing for post-bop "spiritual" or "soul" jazz from the '70s and those records now command money. Some have been reissued. The reissues are OK but often not as compelling as the original pressings even though those were pressed during a low point in vinyl quality in the States.
It is very much a case by case, record by record process if SQ is the issue. I tend to like "less produced" sounding records but you'd be surprised- one engineer said you'd be surprised how much artifice and studio manipulation (post production) goes into making something sound "natural." There are certainly labels that had some great output- Warner Bros, during the "green label" era released some great material- they were an artist friendly label and had very astute in house producers. Some of those records were very popular and sold in large quantities at the time of release and could be found in used bins in record stores for little money. (Used records have gone up in price in the last five plus years).
In some cases, the original records are simply hard to find now in good condition. Alice Coltrane's Ptah, the El Daoud was last pressed in 1974. It is going to be reissued and I believe the reissue will come from a digital source. Will that be a lower SQ end product? Maybe. But you would have to be patient, lucky and probably pay several hundred to find a decent original today. So, you pay your money and make your choice. (I found a copy from its original owner from the year of first release- it wasn't cheap at the time, but the price of that record has easily doubled or tripled since I bought it).
I'm not someone who buys as an investment. I buy the records I want to listen to and treat the whole thing as a process of discovery. I did just get in Chad's reissue of Tull's Stand Up and will be curious to compare it with my UK first pressing. That can be fun too. FWIW, quality control is also all over the place- you hear horror stories of new, expensive records that come out of the shrink with fingerprints, or worse, irreparable damage due to bad pressing.
So, I'm not sure you can make general assumptions across the board for older v newer records. I'd focus more on what music you like, which artists or supporting artists seem to appear on the records you like and research what other records they appear on- for example, there is a bassist from the period--Cecil McBee-- who did a huge amount of work in the '70s and appeared as a side man on a lot of records. I'll buy pretty much anything McBee played on.
You find your own path, compare notes with others, learn and keep learning....