I have a smiley-face sticker on my Pod right now, and I haven’t been a kid since the 1960s! I think that Pod painting would go over well (although I agree that you should use non-toxic paints like you might find in a school supply store), but do not overlook the sticker idea. As an adult, I would not want to sit and have my Pod painted, but I would purchase a fun sticker to put on it while I walked for JDRF.
I think pre-made stickers with clever sayings on them (which you could produce on a computer) also would go well. Maybe stickers with sayings like, “Pancreas: 2009 Version” or “Hi! I’m Pod. What’s your name?” or Insulet’s logo: “No strings attached” would work. I am sure that others on this forum could come up with much more clever sayings than I can at this moment.
Go for it. Your Pod-painting idea is excellent, and it would be a fun, unique way to raise research money for the Foundation.