Plan of action for propagating/repotting?

I have my way overgrown buddy here and Im trying to plot out some moves to make this spring/summer, looking for advice going into it. As a note, yes it's like two trees grown together into one by now.

Firstly, I bought this new pot and it turned out WAY bigger than I expected. Do you think this is way too large of a jump up to repot into? I know its super cramped/root bound in its current pot, hoping if I put a ton of drainage the new one might work…

I also want to either chop/prop or air layer the main branches. Any advice here? Could I air layer both main stalks simultaneously, or is it better to space them out? Should I avoid air layering and just chop em?

Thanks for any help/wisdom, trying to get this dude back in shape and looking it's best!