This totally reminds me of the video from a year ago that was something along the lines of challenging an Olympian. The video showed Levi Leipheimer changing a rear flat. You could tell immediately he wasn't sure how to get the rear tire off & had trouble. Took him 50 minutes. Made me feel less bad.

I read through this rather fast... have you checked your rim tape? I destroyed mine changing a couple of flats and had to have it replaced. I had the LBS do it when I finally put on puncture resistant tires and it didn't cost much. I haven't had any flats since last December or so when I got the new tires (Specialized Armadillo Elite).

I almost always ride alone, but I stick to roads where I know there is likely to be other cyclists just in case I have an issue. It is out in the country, with only a little traffic, but my hope is that one of the other riders might ask if I need help if I did have a problem. Luckily, I haven't had to test this theory yet.