Oh, I agree, the context of her life allows her to lead a life without consequences. I also found that her calling herself broke and struggling bothered me, but at no point she says (not that I remember, correct me if I am wrong) she survives by merit only. Perhaps she states that she wants to find her way in life by her own hardwork/merit, in the sense that it was not a handout.
But I would like to point out that all the advantages she had in life were not the result of wrong doings, so the use of privilege as something unfair bothers me a little too and I do not think the show states that Rory believes she is getting by by her own merit. What she wants is to be hired because of her resume and accomplishments, but I do not have the energy to initiate a debacle on what meritocracy means, not today at least.
PS: I hope the baby’s father is the Wookie guy, something that bothered me is how she loses her values by being the other woman and being ok with that. In fact, I am rooting against Rory because of that hahahaha (oh, I hope Logan gets screwed too, more than Rory even, what a scumbag).