So...I couldn't help myself and completely redid the PCB from scratch. The header should be aligned now (had to modify my footprint with the anchor in the center). For the 30 pin variant of the oled i had to remove one of the unused pins; we'll see if that works out. Something else that needs to be seen to be tested out is the slot for the oled's flat flex. It should be large enough to get one "wing" in at a time, but no promises :s