Earlier quoted context omitted.
I tried jogging over the summer for the first time in years, but my feet started hurting. It would take days to recover. I gave up after 2 months. It feels good but I seem prone to injury.
According to Wikipedia, 10% of all people get what's called "Plantar Fasciitis" at some point. In my late teens, I began to have very bad bouts of this syndrome, whenever I sprinted. The more I ignored the pain, the longer it would take to heal. In my early 20's, I suddenly took up running--eventually ratcheting up my route to 7 miles--after being somewhat sedentary for a couple years. The result of this was perhaps…
For me just changing shoes with a 6mm difference in heel-to-toe drop was enough to create the same problem. I woke up one morning with a pain that felt like a nail being driven up into my heel. I spent about an hour doing deep tissue massage on my arch and calves - did a workout the same day and didn't have any issues the next morning.
You probably don't need quite as much support as you might think if you were willing to slowly remove support which would strengthen/stretch the muscles around the heel.