I did watch his guest-starring on HSMTMTS and while he, unfortunately, remained clothed (the role took place in an airport) I got the feeling we might be seeing him again. He'd fit in great if he's joining the show for the next season (yeah it hasn't been announced but with the popularity of the show and Joshua in particular it's just a matter of time)
 
The guest role was suggested by a former 'Andi Mack' producer to reunite Asher with his Disney Channel co-star Sofia Wylie.

I think if his schedule allows Asher will likely return for a guest role in season 3 where they can have a will Gina choose Ricky, EJ, or Jack storyline

Asher said in an interview “Hopefully we have another recurring spot for Jack in the future"