I've been thinking about naming that slingshot kid Bart after Bart Simpson (since he owns one). I've been picturing him slinging a few rocks at Mr. O' Ninetails' house and maybe even breaking a window or two. Mr. O' Ninetails: Rotten little punk! Off my lawn you should get! Or a whippin' you'll get!
Ooooh! Wonderful headcanon indeed. So if (IF) he'd possibly soften a little after Smithy's gone... maybe Bowyer would have two step-grandpas, a Toad toymaker in the Mushroom Kingdom and a Whip in the Factory. Or a step-grandpa and a step-granduncle.