It depends on the individual cobbler. I live in a place where everyone owns cowboy boots, so plenty of boot makers will tailor, but it does not come cheap. Most shoe repair places I tried won't touch jobs like that.
I feel ya on the strong calves, and no, no shape wear is going to slim the muscles of your calves. Even really heavy people rarely have flab on their calves (ankles yes, but not calves), those calves are very muscular to hold up the extra weight. I went to a university on a hill. You could tell the freshman because they were the only ones with skinny calves.