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@Oswald
Headset .. Personally I'd trim the fork slightly using a file. If you try to saw then the blades going to be on the edge of the tube when you take into account the material lost by a saw blade width .. which is going to be a tricky cut. The rubber is there to make a seal to the stem, which you'll loose if you remove it and potentially you could get ingress into the steerer tube. Other alternative is a 5mm small 1inch silver spacer under the top nut?
Rear drop out screw .. Bad news. Saturate in plus gas or similar to try and make sure it's free then if your lucky, using an undersized drill as you start drilling the screw threads out on the drill so you don't have to actually drill it completely. That's the only option I know .. and I don't like doing it!