Since Rebecca moved, I wonder if Randall ever regretted telling her she should "call first" that time she and Miguel dropped in on the way home from the theater.
As for that dreaded "entry level" position, I think TV screen writers tend to view the working world through their own special lens, one that thinks any job that's not artistic and creative would be hell on earth. That's why we have, in one show, two singers, an actor, a dancer and a councilman (sort of show bizish.) so Rebecca having to work in an office is bad enough but entry level with not even a big desk or a secretary of her own. The horror.
I think Rebecca should have been job hunting a few weeks after Jack died, telling Randall that she insisted he go on to Howard University, even if she had to lie and say she would recover faster if she was busy and on her own.