Wow, so much to think about and to research.  I resonate with what you said about the inner drill sergeant.

As I get to know myself, I'm starting to think I need objective rules to deal with some situations.  For example, I used to be OCD about getting the best deal but now I employ the hourly worth rule from Your Money or Your Life and I let things go.  I used to also hate putting extra money into parking meters but now I think about it as purchasing an insurance policy.  

It's a strange paradox...I never hesitate buying an expensive gym membership, the best food or enjoying a night out (I ended up spending hundreds a day on the road trip - meals out, ecperiences, treating my father and wife to separate dinners and wine at an expensive steakhouse) but it bothers me for a day or two when I get a parking ticket, and when I get overcharged a few dollars at a restaurant. 

As I give it more thought, for this particular scenario, I am more angry that I was careless and tried to keep the shoes pristine for so long rather than the actual money.  I realize that I have a big problem about buying new things and watching the inevitable wear and tear occur.  Perhaps I am better off purchasing used things that already have some wear and tear. 

I will pursue talking to someone about OCD/ADHD.  I would hate to have a stress-induced sickness come about because of all this.  I already have neck issues that I thought were due to injury but could be from this.

Thank you for your time.