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Damn. If you’re looking to replace the cottered cranks, get hold of some old pins (60s/70s NOS) if you can, they’re far better. But you’re still into the tap tap tap, file back, tap tap tap & screw tight, ride for a mile or so, tap tap tap screw tight, etc. stage…
Can you go cotterless without too much pain? Or are you looking at Raleigh 26 tpi threading woes? My Raleigh Twenties are all about the Phil rings and un71/2 bb conversions. But I gather the cost of the Phil rings is now obscene.
You can also unscrew the nut a half turn, tap a bit with a nylon hammer, unscrew, tap, rinse & repeat- I have done this and kept the pins in the past.
Edit: and all the plusgas/gt85/wd40 before doing this