I've been meaning to reply to this for several days, but am just now sitting down to do so... I soooo enjoy your process - this has been motivational and inspirational. Thank you for sharing!
#1 vs. #2: I have a poison eye for Birks. I know everyone loves them, but they're just not my thing, so take that with a grain of salt when I say I like the first picture better than the second. Cute outfit though, love that skirt! It fits you nicely and looks very comfy
#5 I like the silhouette, but for me, the too-low neck and the low-cut armholes would drive me insane. Clothing that you fidget in or feel uncomfortable in, or have to keep adjusting, is a deal-breaker in my book. I would find a replacement for that top that you feel happier in.
I like your other looks I look forward to seeing what happens next! More colored tops? Adding some smart casual items?