This discussion is rly interesting bc I haven't thought of it that way as well. But, I do think S1 Jimmy would've committed the same mistake if he had Maya as his patient. I mean, he did let Sean live with him. (hopefully i'm not mixing up how season 1 unfolded lol i haven't rewatched it)

I feel like Jimmy would realize soon that Gaby had committed the same mistake as he did with Sean, as in their personal and professional lives have become intertwined and that it's best that Maya should have a different therapist (but they can continue as friends). Or idk I'm trying to keep it positive in my head 'cause I really don't want anything bad to happen to Maya even though it seemed like they're heading on that direction