Often I've wanted to automate something, just to avoid some clicks and survive the tedium. Never was it really worth the effort of learning some crazy scripting tool.
There is nothing like a job assignment to get you in the mode to explore new ways to accomplish a goal. I'm sure everyone is familiar with the awesomeness that is AutoIT. It is certainly simpler to understand than VBScript, but if you're wanting to learn VBScripting I would highly recommend you start with AutoIT. It helped me better understand VBScript so when you look at a VBScript example it might make a little more sense.... maybe....
So 3 automation tools I recommend for the scripting junkie.... AutoIT, VBScript and for web automatiion I like Sahi.
Personally I like to see code that make stuff happen rather than a GUI wizard that just does the work behind the scenes.