I'm suprised your therapist would have suggested that you "go all out". Actually now that I wrote that, I take that back, sort of. Way back when I complained to my therapist that I hated a particular skirt and top combination I had. I'd actually never worn the two together, but I dreaded how they'd look. His reaction was pretty much the same, how do you know if you don't try it? It turned out it was a decent combination.
So, forgetting what anyone else thinks, what do you think? That's the real point of the exercise. You can't really compare pre-HRT with any time on hormones so just ask yourself how does it make you feel and worry about passing or not later.