So, how do we handle people who don't quite hit the mark? For instance, the OP's premise is Raffi is not "Roddenberrian" which strikes me as well, not living up to a preconceived standard, rather than meeting people where they are at and helping them out.
As a counterexample, I would say that Barclay is not very "Roddenberrian" in that he is socially awkward, to the point of avoidance, and hiding out in the holodeck, to the point he prefers holoprograms to real people. He is avoidant, similar to Raffi, but his perhaps is not as noticeable. So how do we frame that idea, within this concept of people becoming better and how to we engage them? Because I'll bet that Raffi already feels likes like an outsider and treating her as outside the ideal only would cement that opinion.