I think there are meaningful differences even with older or less than perfectly recorded albums/streams. You will still hear things more clearly.
If you want to go from, say $7k to $14k for a pair of speakers is up to you. You should listen to some music you like and see if you think it is worth it. It is also probably a good idea to make sure the system as a whole is balanced. I would for example probably not buy $14k speakers to a $1k amp unless I intended to change that soon after.
If you are going down in price you can also try some of the new active speakers like Dutch & Dutch or Kii Three that have almost everything in the speaker and just needs a streamer or similar to play.
If you want to go from, say $7k to $14k for a pair of speakers is up to you. You should listen to some music you like and see if you think it is worth it. It is also probably a good idea to make sure the system as a whole is balanced. I would for example probably not buy $14k speakers to a $1k amp unless I intended to change that soon after.
If you are going down in price you can also try some of the new active speakers like Dutch & Dutch or Kii Three that have almost everything in the speaker and just needs a streamer or similar to play.