I love subverting archtypes, too, and I think something that really helps with that is thinking of what playbook you want your character to transition to. Some playbook transitions make sense, like a Touchstone to a Hardholder, or a Driver to a Chopper or something, but the really unusual progressions can make for some very interesting and subversive characters.
I played an Angel turned Savvyhead who began to lose perspective on what makes people different from objects. I GMed for someone who was an Operator who turned into a Brainer because of another PC having a bad effect on him and breaking his psyche. I've been wanting to play as a Faceless who becomes an Angel but retains his plague doctor mask and wants people to be afraid of him for fear of getting too close to someone.
So yeah, pick an unusual playbook combination and try to think of why a character would develop like that. Why would a Hocus become a Gunlugger, for instance, or what would make a Quarantine become a Maestro'D?
Oh, and as a side note, the idea of a Savvyhead whose workshop is a garden is fantastic.