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boston - great bike scene, loads of good people, great (vegan) restaurants (Grasshopper and TJ's, best vegan food on the east coast!).
dc - i dunno, grew up there, and it's lots of fun, good music scene, lots to do, close to the wonderful outdoors that is virginia
philly - good arts scene, bike scene, music scene, vegan food. too small though.
chicago - never been, but always attracted me...
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maybe not enough spacers between top cup and stem, or stem and top cap? if the top of the steer tube is coming in contact with the top cap, then no matter how much you squash/tighten it, you'll just pull the starnut out, and you'll still have play in the headset. put a 5mm spacer in there and try again?
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shit that went for a lot...