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1, yep you can by squeezing or stretching them, I think velo orange have a good tutorial on it.
2, I've never loctite mudguard bolts, and never found they've come loose. I've also never cleaned an eyelet tbh.
Should I be doing that? Never had any trouble when removing / installing guards over the years. Then again I mostly just leave them on even in summer, good for the dust etc.
My mudguard troubles continue :
1°) Is it possible to slightly re-radius stainless steel mudguards? My Berthoud fender cracked at the seatstay due to poor installation on my end. I had put it under tension with the stays instead of re-radiusing it by pulling the edges outwards, as instructed by Weigle et al. (I was actually removing the fender to do so when I noticed it was already cracked).
I tried my hand at re-radiusing it after the fact, and it wouldn't budge. In your experience, is it something you can't do with stainless steel mudguards due to the ductility of steel? Wondering if I should buy aluminum mudguards next.
2°) The eyelets at the seatstay bridge and chainstay bridge are pointing towards the hub, like on fancy custom rando bikes. It's pretty, but as someone who periodically removes mudguards, it's also a pain in the ass, as I have to clean every eyelet with alcohol then slather every bolt with loctite everytime I put the fenders back on, to make sure the bolts don't rattle loose.
I'm thinking of having the holes drilled throughout, so I can put a nylstop nut instead of relying on loctite. Aesthetics aside, is it a bad idea?
See the pic below for a better idea, though I won't put a pretty wingnut.