Here's a bunch of challenges this project ran into, and how they were overcome.
Problem: How can you organize a whole student body to work on a large project?
Solution: Break it up amongst the dorms. Each dorm had their own leadership so that the main organizer had specific points of contact at each dorm, making the whole project easier to manage. There were many residual benefits from doing things this way (i.e. building dorm community, allowing for new leaders to take initiative, encouraging inter-dorm communication... I could go on and on)
Problem: Now that the project is broken up, how do you make sure everyone is on the same page?
Solution: Create and use an email list. In this case, rube-goldberg-l.
Problem: How do you make sure something doesn't blow up and the main organizer doesn't get into trouble.
Solution: From the get go, people are made aware that they have to follow the rules in the student handbook. Additionally, every dorm's leader(s) had to get the go ahead on their plans from the main organizer and Dean Chris. This was usually done during a short, informal meeting at dinner. A dorm's plans didn't need to be perfectly planned out, these meetings were mainly to make sure the big ideas that people had weren't dangerous.
Problem: Where's the money going to come from?
Solution: Four sources were tapped, on suggestions from DOS: Alumni Association Board of Governors, ASHMC, DOS, Shanahan Student Projects Fund
Problem: Since money is only available through reimbursements, how can people use the money on their builds?
Solution: Every dorm is given a budget, and dorm leaders are in charge making sure they don't go over that budget. People who buy materials are in charge of submitting their receipts to the DOS office, which will handle the reimbursements.