I hope the pain in your heels is not Plantar faceitis (sp). I had that and that was probably the worst thing I have ever expierenced. I didn't go to a doctor for it for about 3 years and never have had any other thing wrong with me, so that is probably why it was the worst.
Anyway, a cortizone shot into the bottom of my foot made things much better.
Since then, I found that Wolvering boots fit me better than any other brand. I think if you find a good pair of boots that fit, most of your problems will go away. for me it is Wolverine.

Wingmaster