Now I have one of these about to be shipped:
A Roe Racing Triton, with Don't Trip Poppys, Riptide bushes, and Big Zig wheels.
It's a dedicated LDP board, ie Long Distance Pumping. The board, trucks, wheels, and bushings are carefully set up for pumping. I'm hoping to be able to go for a night pump session 3-4 times per week for fun/fitness. I'll be logging with GPS. This is a fairly new sport in Oz, pretty unknown, but the yanks can hold steady averages between 20-35kph while pumping.

I haven't named this one yet...
To answer your question, Saltiest, I'll wear a helmet while doing LDP for sure.
For the rest, I'm just pushing/carving slowly around the neighborhood, haven't had an off yet where I couldn't just jump off & run it out.