Thanks for this, it's a great article. I have this problem with my boss occasionally, which is funny because he's a programmer. "Oh, you just have to do this and this, shouldn't take you too long."

You're right, there's always those bottlenecks that crop up that you didn't expect. It's impossible to truly know all the limitations of the software you're working with. I work with Drupal, and it has A LOT of those problems. Sometimes I'll think something will be easy to do, only to find out that the popular modules I thought would work great don't cater to the specific use-case I'm working on. Then it's back to schlepping.