Are most recordings so bad it's not worth spending large on speakers?

This is nuts. But not for any of the reasons given so far. This is nuts because its not just the speakers, or any of the other stuff mentioned- its ALL of it. Everything matters. If its not worth having good speakers then its not worth having good speaker cables, amp, interconnects, turntable, cartridge, phono stage, power cables, power, and room. If its not worth having good speakers then you can just pack it all in right now.

Not to mention, he's in the speaker business, telling you not to buy speakers. This Morrison sounds like the kind of guy makes you wonder what is wrong with audiophiles.

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Define bad.

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.

Even some old active speakers might surprise.