I have to assume the fender roller exerts an outward, and maybe simultaneously upward force on the fender lip, probably in reaction to an inner force it simultaneously exerts on - what - presumably the frame? Or maybe the axle flange?
My only advice would be to do this slowly and very gradually in repetitive passes. The danger is that if you exert too much force, you may buckle the fender in a way that would take major bodywork to correct.
About the logo: is there any way you could make it yourself and attach it permanently to the flat, central hub covering of the rim? (The backing material and the ink used would have to be waterproof and UV-proof as well.) Maybe there's an online source that would make this logo for you with a very strong PSA backing, like a sticker, similar in consistency to the body stripes GM used on the sides of the car?On edit:
Just found this possibility:https://www.stickermule.com/products/circle-stickers