If you want lots of examples of really stupid shit that software developers (and other IT people) do, go read The Daily WTF (http://thedailywtf.com).

Or get a job at any software shop that does a lot of work with abandoned projects (e.g., "Help, my previous developer left me in a lurch, can you finish up this PHP e-commerce store customer management system database driven enterprise solution?")

I'm not much of a rails developer. I refrained from describing what constitutes "stupid" software development since everyone's heard best practices lectures...