So with that being said, I'd encourage you to check out a book called Thinkertoys[1]. Although it's a little elementary at times, it lays out specific techniques to get your creative juices flowing. Its great for analytical types because it provides a concrete framework for a very abstract activity (idea generation).
--- [1] http://www.amazon.com/Thinkertoys-Handbook-Creative-Thinking...
Thinkertoys (http://www.amazon.com/Thinkertoys-Handbook-Creative-Thinking...)
and
They're both among my fave books of all time, though they are relatively similar in content so getting just one is fine.
They cover a lot of different strategies for thinking creatively and outside the box, provide tons of examples, and have a lot of exercise that you can try yourself (and while it sounds cheesy, the exercises are actually fun)
- Simple Heuristics That Make Use Smart by Gigerenzer, et al. (http://www.amazon.com/Simple-Heuristics-That-Make-Smart/dp/0...). I have heard good things about this book but have not read it yet.
Category 2:
- Think Twice by Mauboussin (http://www.amazon.com/Think-Twice-Harnessing-Power-Counterin...)
- Influence by Cialdini (http://www.amazon.com/Influence-Psychology-Persuasion-Busine...)
Category 3:
- You already mentioned Michalko, but his other book, Thinkertoys, is also very good (http://www.amazon.com/Thinkertoys-Handbook-Creative-Thinking...)
Category 5:
- Switch by the Heath brothers is excellent (http://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385...)