To answer your question, yes you could be disappointed with analog sound compared to the digital that you are used to. And much of this will have to do with your expectations.
But let's take off our anal audiophile geek hats for a second and look at the eventuality a different way. As a classic jazz fancier, you are surely aware that there are many, many great performances that are only available on LP, just as there are great performances only available on CD. Why would anyone who is genuinely interesed in the breadth and scope of our musical heritage intentionally cut themselves off from a substantial amount of great music? Real music lovers will want to have the ability to access both formats, and sound quality be damned.
But let's take off our anal audiophile geek hats for a second and look at the eventuality a different way. As a classic jazz fancier, you are surely aware that there are many, many great performances that are only available on LP, just as there are great performances only available on CD. Why would anyone who is genuinely interesed in the breadth and scope of our musical heritage intentionally cut themselves off from a substantial amount of great music? Real music lovers will want to have the ability to access both formats, and sound quality be damned.