I agree with Mothra, there's no simple rule about it all. I have some LPs that were originally digitally recorded, and they sound really good. They're maybe not quite as warm and mellow as a full analog chain, but they are very musically satisfying. To paraphrase Michael Fremer, with a digitally recorded LP, you're hearing an analog master made from a pro-quality ($20K and up) D/A converter working from the original sampling rate and word length. With a CD the digital master has been dithered down to 16/44.1. The LP sounds better, period.
As to digital RE-mastering, I'm not sure. Some probably make things sound clearer, some may make them sound thinner. I have little experience in LPs made from digital remasters.
But I have a few digitally recorded LPs and I like them. These include the soundtrack to O Brother, Where Art Thou?, a digital Angel direct-metal-mastered LP of The Planets, and a Fantasy jazz LP of Hank Crawford and Jimmy McGriff. All sound fabulous with the warmth of LP AND the sparkle of digital.
As to digital RE-mastering, I'm not sure. Some probably make things sound clearer, some may make them sound thinner. I have little experience in LPs made from digital remasters.
But I have a few digitally recorded LPs and I like them. These include the soundtrack to O Brother, Where Art Thou?, a digital Angel direct-metal-mastered LP of The Planets, and a Fantasy jazz LP of Hank Crawford and Jimmy McGriff. All sound fabulous with the warmth of LP AND the sparkle of digital.