Just cherry-picking another detail from this article:
http://www.heraldsun.com.au/news/victorian-skier-reported-missing-in-canada-last-seen-in-whistler-hotel/story-fnstek7z-1227341572753
Jakes stepdad Kevin Raymond told the Herald Sun the teen had left some belongings in the hotel but had taken his backpack and some clothes.
So from the various articles we've found, we know that he took his skis, his backpack and some clothes, but he left his ski boots. Most people wouldn't leave their ski boots behind, they are expensive to replace. You can't ski without your ski boots, and since he's short on funds, I don't think he's planning to rent boots or buy new ones. Yet, Whistler's ski season is not over yet (ends June 7), and if he's there skiing, or maybe plans to go to Mt. Hood in Oregon (the only other ski area open now), he'll need boots. I suppose he could borrow some boots, but most experienced skiers don't do that because they wear custom-fit boots (in fact, most experienced skiers don't rent boots either, unless they absolutely have to, because a bad fit = very sore feet). I realize he's 19, and maybe he doesn't care about his boots fitting properly, but the teens and young adults I know who would go on an extended ski trip like this love their boots as much as their skis. All that said, I'm suspecting that if he skipped town he has no plans to ski again before the season ends.
If he heads to the U.S., as his family mentions he might, then he'll need to use his passport, so at least he can be tracked that way. I would imagine officials are already checking on that now that his parents have said he might have left Canada.
I wonder if he has a cell phone so they can track him that way? Has he used it recently? I also wonder if there's been any activity on his Facebook page. The last thing he did viewable to the public was changing his profile photo in the beginning of March. I would think his family has contacted his friends to see if they've heard from him. I know that's the first thing I would do if my son disappeared, especially since he's in a foreign country.
If they don't find evidence of him leaving Canada, and don't find evidence of him using his phone or social media, I would be concerned that something happened to him that night he left the hotel. If he was planning to leave town, surely he would have wanted to hook up with some friends to say goodbye and share a few drinks.