Actually wait....I do have a boot suggestion. I have UA Valsets. They're lightweight and feel like Nike Frees if you've felt those before. Super comfortable on my heal, can walk for days in em. As a result they are not heavily structured. That's not what the boot is made for. They won't...
No advice on the footwear, but check out two things. Check out achillies bursitis and haglunds deformity. Could be your Achilles pressing against your slightly more pointed heal bone (haglunds), or it could be the bursa just underneath the achilles and not the achilles at all. Just a couple...
Dense woods....rolling hills.....made me smile. I'm from Missouri, moved out to WA years ago but I go back to MO to hunt with family every year.
Bringing them all out here would be pretty crazy for hunting Elk. They'd be amazed.