Will's claim to being finically secure is for setting up a promising travelers program where he uses his millions of dollars earned from Level 1 to pay for his trips in the van. The only reason Andy is making it through these financial struggles is because Will stopped lending him money and he started panning for gold on his free time. He got lucky after finding moon rocks wedged between Ian Compton's teeth, that he sold to Yoke Collection for an ideal life time sponsorship with the addition of receiving a gazillion dollars. However Andy is a humble man and sticks to his roots of looking dirt cheap and the only reason he dosent compete in x games is because he has to keep his street credit constant with the image of being an average skier like Steve Stepp, otherwise the olympic slopestyle competition world would be blown away by the awesomeness of hippie killers and zero turns off jumps. People like Bobby Brown, Nick Goepper, Henrik Harlaut, McRae Williams, Kai Mahler, Alex Schlopy, Gus Kenworthy, James Woodsy Woods, Torin Yater-Target, Matt Walker and those french guys or whatever from superpipe would all have to pack their bags and leave the sport because there would be no point in competing against somebody who scores perfect on every run. Andy would let tom stay in the ski industry only because he taught him some afterbang in episode 1.4 but would make him promise to never do a tripple even if he added style to it by basically doing a 180 to switch tripple. Tanner Hall could also stay in the industry because he is a great influential speaker and he will push the sport to the next level and get Andy in the history books even if sports center completely ignores Andy's wizard tricks directly after xgames big air. If only Will wasn't such a money hog Andy would have never became rich on his own accord and the traveling circus would have less episodes, for Andy would still be working at pizza hut, because sometimes you just need a job and he is a normal person.