I am not going this year, but I can answer any of your questions. As for the ride in, ride out... Parking is pretty secure, as in, once you are in pikes peak, you are in for the duration if you have gone above the start finish. We have never worried about our gear in the team truck, but they did bust some people that were going through unlocked vehicles. My only worry would be if you went up to the cove or devils playground, you may have weather. By "weather" I mean anything from clouds to a blizzard. It really is ride at your own risk, with that said, though, I wouldn't want to go up the mountain any other way. Personally, I would view from the lower half and do some hiking. That way you can get off the mountain if it fogs in and they stop the races.