I don't recall exactly but I think it's the level of the Persona more than Joker himself. When I did NG+ with this custom Arsene, I was doing pretty high damage for the level Joker was at most of the time but I also was keeping my Arsene maxed out in the stats I wanted as I played.
Apt Pupil raises crit chance? Then yeah, it should be possible. I had it on my Yoshitsune as I transferred it over from Futsunushi. I had a huge crit rate with the skill, something like 50-60% of all attacks I did with Joker was a crit.
Some skills cannot be transferred to other Personas. I tried to get Hassou Tobi onto Arsene but he couldn't learn it or it wasn't transferable to anyone.
Also, in regards to Yoshitsune,
END GAME SPOILERS so don't click on this next link unless you've beaten the game or are on the last boss
This is my favorite thing in my entire run of the game. I'm so glad I was streaming to catch this moment because it was amazing. It was all because of Yoshitsune too, lol.