Eric, you might look at zappos.com and check out the Propet "Camp Walker". I don't have the heel problem, but I am hard to fit--to the point that Russell Moccasin couldn't help. You know about my other problem.
I was leery--the camp walkers are only $64 (shipping included), but I gave them a try. The day I got them I walked about 4 miles, mostly on gravel, mostly up or down hills.
They are soft--didn't have to break them in--and I didn't have any blisters or sore feet of any kind. Ankle support is excellent. They do run a little wide--I normally wear a 4E, but the 3E fits perfectly. They also have free return shipping if the fit isn't right, and a 6 month wear warranty.
I've had mine less than a month, but I'm very impressed so far.
Chad