Awesome thread! The only ones I haven't gotten are:

Mashin' Potatoes: Lol, I live in south Louisiana... no hills
Flyin'/Rocketman/Reckless endangerment: Lol, see above
Ultimate/Hahd Baastuhd: couldn't finish the ride with a broken femur.
Frosty: Lol, see #1 and #2
Pragmatist: no cabs here.

I'd humbly submit these as additions:
Double Whammy: Flat both tires at the same time
Litterbug: Lost pump/water bottle/whatever somwehere on the way
Follow the White Rabbit: Chased by a big dog
Tastes Like Chicken: Got caught by the dog
Who Let the Dogs Out: Chased by multiple dogs