A word of caution: It is possible to get so caught up in automating and other meta-work that you lose focus on the object-level goal. I know this because I've done it.

"Oh, I could probably automate this with a script...you know, I should really optimize my vim setup for script-hacking...you know, I really need a way to keep track of my vim plugins...I could probably tweak these plugins to work better with what I'm used to..."

A lot of these time investments end up paying off (e.g. you really should use vundle to manage your vim plugins), but every now and then you should push through at least a bit of tedium to make sure you have a good idea of the problem, how much pain it's causing you, the scope of similar-enough problems which are likely to have the same solution, and exactly what you need to do to solve it.