I think must Rebb’ish kids are proud of their status. It really depends on how good a job their parents did in instilling pride in them. It’s similar to Yiddishkeit when living really OOT or when frum kids went to Public School and stuck out. I understand it’s different to an extent because these things are family customs, not Halacha, but I hope you get my gist.
The other reason most Rebb’ish kids are indeed happy with their lot is because of the kavod and perceived higher status which sort of compensates for a harder lifestyle.
But regarding learning English, he can have boys in Yeshiva teach him or find another way if he really wants to, being Rebb’ish doesn’t mean he has to forgo that, IMHO.