Just decided to jump in!
This thread inspired me to get off my bum and move - DH then challenged me to go to disney - for the HALF MARATHON - this thread was my motivation - I'm signed up to do my first race - EVER, a 5K on sunday (Chicago Montrose Harbor)
I am in my 40's and 40#s overweight - horrible... I have lots of negative talk in my head as I "wog" (jog at a walking pace!) I too have heel pain - very severe plantar fascia - running shoes designed for my style of feet (I pronate too) I didnt think would make a difference (they are$100

) The doctor said orthotics will help ($300) I decided to go with the running shoes - I went to a running shoe store - where the people there are knowledgable - it made a huge difference - they even reccommended orthotic style inserts (Power Step I think $30) IT WORKED for me!!
I still get pain, but there are foot exercises I do - that helps - I have to stretch that tendon muscle - really keep at working it - even using a hard tennis type ball and rolling it under the heel - and ice works too to bring down the swelling...
On the Wish forum running/competition there is a sticky there with lots and lots of amazing websites - I love the gmap pedometer one - I get a view of the area I'm going to wog, and I plot out the distance - plus I do use a pedometer!!
Walking down the stairs after my longest wog ever in my life - 5 miles - was miserable - total and complete pain, ankles, knees, bum, and back...
But that day has passed, and I'm working on today. Just for today I'm going to get out there.... my final prize will be a trip to Disney in January!

If not for that, I'm sure I would've given up long before now!!