I wish I had a firmer understanding of what is meant by "boot problems." I certainly don't doubt that Kevin has been plagued by them, and I sincerely believe that he has tried to remedy the situataion.
But I also struggle to figure out what it is that can't be fixed over the course of years.
Is it an equipment problem with the boot itself? Is it some sort of injury or something that makes all boots uncomfortable or doesn't give him confidence?
Edit: If the boots don't fit, why not get a new pair? I'm sure it would take time to adjust, but years?
I suppose if I were a serious skater, I'd understand. But, I'm not. I know you offered some insight, but I'm too green to follow the line of reasoning.
Kevin got several new pairs of boots, both stock and custom made over his years of boot problems.
I think skaters can have several different problems with boots:
- they make your feet hurt (that trivializes it; how about "cause excruciating foot pain")
- they fail prematurely: heels break, boots rip, sides break down, etc
- technique is lost (example: Underhill/Martini: if they had realized there was a problem she wouldn't have worn the new skates at the Olympics)
I think Kevin's boot problems were in all 3 categories.

. Articulate and informative.