I'd have him flounder trying to find acceptance all over the show. THS. Have him try and freestyle for The Acclaimed but they're too caught up in imploding to hear it. LIJ want him to put a mask on and he can't again because his face breaks out under it, or something.
Just have him fail to find a place while trying to pander toward them.
Then bring Sam in on some 'they don't love you like I love you. Why change to fit with them, when they all changed trying to
be like you?'
Have her be half-Delilah and half-Mallory. He flies high because of her, but also occasionally crashes and burns trying to please/appease her.
So you take him on the natural progression of a kinda corny brother who is great at what he does and terrible at everything else, to a dude who pulled something high and is riding the edge of the blade of crashout trying to prove he deserves her. To us. But mostly to himself.
Everyone can roast him for his argyle socks and shyt, and she can be right there with a louder, more ridiculous pair for next week and unconditional
(as long as he ain't losing) support.
Have it work out for him in some regard.
Then you can start others vying for her managerial services, taking a less... cuckold-y approach to that CJ/Miro angle from before. Dudes chase, and he gotta put them down. But eventually you can give her a women's act to manage. Have him be the only one who gets her ring intros. He'll get the very heat they're chasing for Dom pulling above his weight/look.