I've completed my first week!
Yesterday I did route #3 which is 4 laps around my complex - a gentle rolling hill type walk (2.3 miles). I barely made it around the first time and thought for sure I would stop when I got back around to my front door. It wasn't so much shin pain as it was a terrible sharp cramping pain in the muscle running down the outside of my right calf. This time I had music with me and used it to distract myself, stretched often, and made it the full 4 rounds. Near the end Christina Aguilara's "Ain't No Other Man" got me through.
Today was route #4, a big circular route along pretty heavily used roads (2.2 miles). I decided to do the short uphill portion first. Again, not 1/4 of the way through I got that searing pain. I could barely go more than 20 feet without having to stop. After yesterday's pain I had decided to use the inserts I bought at a walking store a few years back (recommended after doing a test on where I put the most pressure on my feet). Well, after this horrible pain again today, I removed the insert and walked without it (just on the right). This reduced my pain to an ache and I was able to finish my walk fairly easily... I finished in 46 minutes, the quickest yet. Today's "get me through this" song was "Say It Right" by Nelly Furtado (this is my 7 y/o's mp3 player!).
My goal for this weekend is to find a proper insert for my right shoe, let the muscle recover a bit, then start again Monday : )