My fraternity house had a housing license for up to 22 people. We had a /16. Though, my understanding is that only the first /24 is currently routed to the house, and we moved to a larger house that's licensed for 50-something residents.
Recall AllAdvantage.com, which had a pyramid-scheme style payout for installing spyware on your computer and browsing the web. Payout capped after browsing 48 hours per month with the spyware on. One of the guys trimmed down Win95 and bought a student VMWare license. A gig of RAM was about $4k at that time. He scripted everything up so that at boot time, the Win95 guest would mount an SMB share from the host, remove the first line from a shared CSV file containing fake account details, and proceed to register a fake account at AllAdvantage with him as the referrer, and randomly browse for 48 strait hours (using a local caching web proxy) like a meth head on a bender, and then shut down. Monitoring software on the host would see the shut down VM and spin up a new one with a new IP. The VM IP assignment code hopped all over the /16 to reduce suspicion. AllAdvantage went out of business before it failed to ban him. 30 VMs ran simultaneously. In a 30-day month, he had 450 VMs run, and got just under $2 in referral fees per VM. The fake accounts never made enough money to get cheques mailed to their fake addresses, so AllAdvantage didn't get returned mail or un-cached cheques, but he was still very surprised that he never got caught. He figured he had less tan 50% chance of making it 4 months and paying off his 1 GB of RAM. He wasn't really doing it for the money, but saw it more as a kind of cat-and-mouse game.
He was always doing stuff like that, enjoying being the mouse in a cat-and-mouse game, with almost none of it for money. He just got a kick out of seeing people doing silly things and demonstrating the silliness of their ideas. You can get into a fair amount of mischief with a /16, which is presumably why now they only route the first /24 to the house.