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I’m sure I’m making this more difficult than it needs to be.

I’m working on a project where I’d like to remove the “H&R Racing” from the side walls of a set of H&R silicone tires. So far I’ve tried acetone, isopropyl alcohol, and even contact cleaner, and none of them made a dent with removing the lettering. Am I missing something here? What else can I try to remove the lettering? Do I have to sand them off?

Just sand the lettering off...

I rub off the lettering on the Daytona Pro Track tires with a rag (usually an old cotton T shirt) and good old Ronsonol lighter fluid.
Works great and clean every time, especially if you do it before using the tires. Should work the same on Gene's H&R tires, too.
Hope this gives you another option. -- Ernie :>)