I too am Type 1 diabetic (also a late onset). While I haven't done much long range bike traveling, I have done extensive traveling. I have not found it to be a problem having insulin unrefrigerated for reasonable lengths of time (say less than a month), at reasonable temperatures.
Regarding the border crossing, one point is that it may be easier to get across with the medicine in the original bottle, instead of in the cartridges. I've never had a problem, but it is potentially one less thing to worry about.
As mentioned, a glucagon kit is vital, as well as someone that knows how to use it. Also, snacks that can be easily consumed, and are high in carbs, in case of low sugar. I don't really see the point in medic alert jewelry if you are wearing a pump, but I still have one.