I worked IT in a high school for about 10 years. Here are some of the doozies:
- weed stashed in a PC case
- pop tart jammed into a DVD drive
- illicit domain admin account created by a student worker
- script to set porn to be the default background on reboot.
My wife and I use Goodbudget with a single login. It's pretty quick to add purchases as they are made and easy to look through the history and see trends.