Look at experimenting with other insoles. I have a pair of Sportiva boots that look great but I was finding them painful. I very recently removed the thin insole provided with the boots and replaced it with a Karrimor insole from a sale @ Field & Trek. This provides much more cushioning and early results are encouraging. Heel shock is much reduced.
Also look at Ecco boots if you can track them down. If they fit they are very comfy.
28" waist by dieting!? What was the diet? Water? I'd love to get a few inches off my waist. I'm currently a European size 54 or about a 38"+. When I was younger I was a 36" waist and I'd love to get back to that. Or was your healthy living LOADS of exercise?