If someone knows a way around this limitation, or a simpler webserver to require / embed, I would be thrilled. But so far this is the best I've found.
You'd need to tell users to enable file access for the extension though chrome://extensions/, since that isn't enabled by default and users have to opt into it. I also don't know if there is a way to get the current user's homedir without hardcoding it.
Also: you're being super careful to not allow arbitrary reading of the filesystem, right? A good sanity check would be to ensure that realpath() of any file served is under ~/.js before handing it off.
https://github.com/defunkt/dotjs/blob/master/bin/djsd#L26
(Also, Ruby comes with OS X (just like Python) so it seemed a sane choice.)
Sure basic install-ability is great, but I bet you this tool was made to satiate an itch he had, and he used the tools he's used to. Little apps like these aren't engineered. Just hacks, for hacks sake.