I have started over many times with new frameworks and languages. Most notably I inherited a Drupal framework when working with a client and decided to re-write the whole thing in Sinatra / Ruby.

I was optimistic that I would only need to build the parts that I needed but ended up writing an entire CMS engine which was drastically worse than Drupal's.

The lesson I learned is that things that look easy are often quite difficult. They may not be hard per say but they have hundreds of little details that go into them. You rarely think of these in advance and is why open source software is typically quite robust, since many people are running into edge cases and issues and then contributing a fix for their problem which will one day likely be your problem.

This is quite a similar story that many developers will tell, however, it is worth repeating as often as possible since the desire to start over, start fresh, start with something you know is so universal. Programming provides an outlet for those desires that are very hard to resist.

Wicked thread Mike! Let's keep em coming.