Show 'Can’t join a path' message as a soft one
Modal dialogs are very dated. They grab attention, they interrupt workflows, they yell at you. Most times we don’t need these as loud as they are — a whisper is nice.
And Ai actually now has these, 'soft' messages, like the one we get when we modify a live shape — 'Shape expanded', at the top of the view, in a gray rectangle. Calm, non-intrusive, with auto-destruction timer. Nice!
But there are other, legacy warnings and screams.
The most annoying for me persoanlly is the one I get when I try to join a closed path (just in case, to be sure it is closed), but Ai yells at me — 'you caaaaan't' — with a ding and a message and a text... just show the 'Path is already closed' soft message.
Perhaps don’t mix all the cases together and display it as a huge page like you do. A user has a compound path within the selection? Tell it, and only if the user really has it. Same for other art types users can’t join.
I see an educational benefit in having it like this now... but look, if I enable 'don’t show this again' checkmark in this alert box, I won’t be able to see if I should join more or is it just enough.