One note about lighting. The function that most of them are designed for primarily is to be seen by cars. This is why many of them do not illuminate the road that well.

Congrats on the commute, and that is a pretty impressive load of stuff you are carrying.

The pant's size vs measured size is true for everyone. The store sold pants are no longer accurate to waist size (they have a smaller number for the same size waist) and every decent tailor will give you a bigger number than your jeans do.