A practical question then: will he be able to read my OOC message? I mean, he may just bluntly pause and not read it at all - and then it might vanish for him.
It won't vanish.
If he's switching back and forth between two characters, can you send it to both?
In addition: an OOC-friend of him (who plays in the same realm) claims he just cannot decide where to play, and therefore he chooses this method. I assume he sort-of plays in two realms at once right now.
That's not really a valid reason for this sort of abuse of the pause system. If he wants to play more characters, he can donate.