I think you’re asking reasonable questions. It’s one thing to quit your job and go to an accelerated course, flying every day. But flying now and then and taking two weeks off? He probably ought to get a job delivering pizzas at night or something at least.

For you though, try to take the long view when you get frustrated, the potential pay off is pretty good. Getting there is painful and requires sacrifice (as you are learning).

I highly recommend he go straight to CFI, that’s going to be the quickest way to a paying flying job and eventual airline job. With what I’m hearing, I’m concerned about his inertia. I could see him struggling to find a non CFI job for several months (and he definitely needs a non flying job in the interim).