Building your own online transit planner with a bike and a GPS
The catch? The Halifax public transit commission doesn't want to have anything to do with it. They've spent over a year and untold amounts of money trying to do it themselves. And because they're not helping, Will had to travel around Halifax by himself, marking down stop numbers, times, and GPS locations, and feeding them into his database. The resulting database is incomplete, but more complete than you might expect, given that he estimates the data collection was only about 30 hours of work. (Halifax has a population of only about 360,000 people.)
Now, in my experience, once you've made someone look stupid, as Will has unfortunately done with the transit people in Halifax, they'll get even more defensive. That means they'll do everything possible to avoid ever admitting that they've wasted their money and produced results inferior to results you would have given them for free, even if it's clear to everyone that this is the case. In sales, a defensive customer is a dead end, and although I wish Will the best of luck, I expect not much progress to happen.
...in Halifax, that is. On the other hand, there are a tonne of municipalities with exactly the same problem. Sure, Google Transit software exists and does trip planning - if you send them your route information in the right format. But most cities and towns don't have their route information in the right format, and getting it right is seen as prohibitively expensive or risky. Maybe Will has stumbled on an innovative way to solve that problem: get students, volunteers, community members, or any random end users to just bike (or bus!) around collecting the information from its existing sources. If you can make it easy enough for lots of people to collect and enter the data into your system, and then find ways to cross-check the inputs for errors, this is something that could benefit people in a lot more places than just Halifax.
iPhone app, anyone?
ssh+2FA to all your machines, anywhere, without opening firewall ports.