These days, after 50 years of listening to records, CDs, tapes, you name it, my gut tells me the records with unique sonic merit over the alternatives worth investing in are mostly those from the days when analog gear was used solely in their creation, which was often the case through the sixties and somewhat into the seventies after which digital took over.
Having said that there are many recordings from that era even that benefit these days from a good digital remastering. At that point, I'd just go with the digital source material but I could see where newer vinyl renditions might have something unique to offer. But even then, modern vinyl is not a slam dunk soundwise. Its more expensive than ever and quality control became more hit or miss over the years since the early "golden age" of vinyl/analog.
Having said that there are many recordings from that era even that benefit these days from a good digital remastering. At that point, I'd just go with the digital source material but I could see where newer vinyl renditions might have something unique to offer. But even then, modern vinyl is not a slam dunk soundwise. Its more expensive than ever and quality control became more hit or miss over the years since the early "golden age" of vinyl/analog.