The biggest pain point I have with dotfile management is that none of my computers are exactly the same, so if I start pulling dotfiles from a repo I get unwanted configuration on a machine. It could be something as simple as a Vim theme not looking right on another computer because it's using a different terminal.

I guess what I should be doing is adding if statements into all of my config files, but instead I wind up just copy/pasting the parts of config that I like from my github repo and never actually doing real dotfile management. Which just leads to the repo becoming stale.