An Ordinary Object

Hi everyone, I'm looking for advice on hopping programs. I entered my current PhD program with my BA (from a medium-sized LAC) one year ago, with a statement of purpose that I was embarrassingly broad. I've decided on an AOS, but now I want an upgrade. Placement at my (Leiter-unranked, though not unmentioned) program is decent, though in recent (~past five) years it's been bad. When there is TT placement, it's to R3s (or R2s, once in a blue moon). I'll welcome any advice! Here are a few specific concerns. (1) My GREs were 164V (94%), 160Q (76%), and 4.0W (60%). Should I take the GRE again? (2) I have one undergrad letter I can still use, from my department chair who went to a Leiter #21, is professionally visible, and edited a volume for Blackwell. I'm expecting to secure two letters from a prof in my AOS. Is this a good plan? (3) I familiarized myself with Leiter's rankings, and it looks like a good application spread for my new AOI (medieval) would be Toronto, Notre Dame, Boulder, Cornell, SLU, and Purdue. Does anyone at one of these six places have insights about applying to them? Or about the status of their medievalists? And, does anyone know whether Georgetown is a decent option? (4) Are there any embarrassing blunders I should avoid committing as I navigate this whole thing? I plan to apply out this fall, and again next fall if nothing happens. Thanks in advance for the help!