Yep, that definitely explains the angle, as the frame was designed for 27 1-1/4 wheels. That, combined with squeezing the rack arms inwards (raising the platform higher) to reach the narrow canti bosses, is likely what's driving it upwards.

re: using a daruma bolt: the trouble with that setup is that you lose quite a bit of tire clearance beneath the fork crown vs. using the brake bolt tab. I agree though that it's a superior system, so I'll try mounting 35c tires (currently have 32c), check the clearance, and see if it's possible to go that route. That would allow me to add more spacers to the rack bolt on the front of the fork, and get it level.

re: trimming tab to clear headset: I've got it folded back now, but ya could try cutting the top off it, especially if the daruma bolt setup doesn't allow enough tire clearance.

re: bending the bolt a bit: that may be my last resort. It's stainless steel, which can handle a bit of shaping. I know people bend Nitto racks to fit, although I'll wager those are better quality material.

re: my OCD--let's be honest, if you're regularly posting in the C&V section of BikeForums, chances are you've got a bit of OCD! But ya, once the bag is mounted you really can't notice it.

Thanks everyone, I've got a few options to consider.