[IanCal]

> It's ridiculous that I can't document notes on dependencies in my NPM package.json, or add a little reminder to my Sublime Text configuration as to why I set some value

Why not have

    { "keyname" : "aldkjfhaldhfa"
      "keyname_comment" : "asdfjnad" }

If that's not enough, use something other than JSON. Adding comments will just result in it being valid in some parsers and not others.

[sixbrx]

How do you know application programs won't barf if they see an unexpected key?