Great points, all of them. If you're going to carry all of the tools a LEO carries, why not use the tool the LEO uses to carry them?
As for the clothing in disrepair while carrying, I'd expand on that to include clothing that might not mix well with firearms. For example, I have a shirt from a band in Finland named Finntroll. The front is a simple little band logo but the back has a rather humorous comment (for those who know what the band is singing about) that says "Putting the laughter in manslaughter since 1994." The shirt in and of itself can be explained to anyone who is curious about why they're joking about laughter / manslaughter spelling similarities. The firearm in and of itself can be explained with some basic Constitutional law comments and a polite conversation. Trying to explain the shirt and the gun at the same time would not be easy, especially in front of a jury after a defensive shooting.
EDIT: Allow me to add that I never wear that shirt when I'm OC'ing and I rarely wear it when I'm CC'ing either.
Long story short, we all shouldthink very carefully about what we're wearing when we OC. (and I haven't even gotten into gang colors or looking like a Hell's Angel either...)