coffin
When Larry Marten's father passed away, his son decided to build his own coffin. It turns out that building your own coffin is really not that hard after all. It's the bureaucracy that followed that was the real challenge. From the really touching article by Dale Dougherty in MAKE magazine:

He was required to get a permit from the county to transport his father. The woman at the county office said that they don't issue permits to individuals but to businesses licensed to do this work. She refused to issue the permit but Larry refused to leave without one. He thinks that he just finally wore her down and he got the permit.

At every point, he met resistance as though it was the craziest thing they'd ever heard of. Only professionals are allowed to do it, he was told, and there are all kinds of regulations. He was determined, however, and in the end, everyone at the hospital and county turned around and became helpful and came to respect his decision.