The simple solution would be to do your edits using browser toolbox - that should get reloaded "live" while you edit it.
But if you truly want Firefox to reload the file while some external editor is modifying it then that's going to require some serious hackery. Like, writing you own custom functionality using autoconfig that would poll the filesystem for changes for userChrome.css and the reload it if file modification date changes. I donmt see why it wouldn't work, but it's pretty stupid if you ask me. More sensible would be to have a button which reloads the file when clicked - this would of course need to be created using autoconfig as well.