This is a 1954 frame, and I suspect that the fork damage could have happened decades ago. On the steerer tube, you can see where the top edge of the lower head race was rubbing the tube and has worn down a 3 cm wide patch of steel. Given the thickness of this tube, I don't think the 1 mm worn depth makes any difference. If it's really been this way for decades, and I believe it was ridden regularly through most of it's life, then it's plenty strong as is and maybe I shouldn't try to straighten it. It's really a matter of how much money I want to put into it and how much I'm really going to use it. The only way this bike might see much use is if I give it to my daughter and her BF who live in the city and commute 2 miles to school. Just to replace the parts that really need to be replaced (rims, pedals, grips, stem) is going to cost ~$120. Getting the fork repaired or replaced would at least double that. I'd be happy to hear opinions of what other people would do with a 1954 three-speed, whether you'd value it more as original as possible or update parts or replace the fork and repaint the frame or just keep it running for minimal $$. I really started this just as a fun project to learn from and keep me busy.
Oil is good, grease is better.
2007 Peter Mooney w/S&S couplers/Terry Butterfly
1993 Bridgestone MB-3/Avocet O2 Air 40W
1980 Columbus Frame with 1970 Campy parts
1954 Raleigh 3-speed/Brooks B72