I'm a fanboy when it comes to Github's work culture. After reading this blog post by Zach Holman, I wanted my company to have a cool chat bot that people could easily hack on. However, one major obstacle to this dream was that our company's de facto communication platform is Skype, which isn't the most hackable platform to be found on the interwebs. As it turns out, there used to be an officially supported Python library for controlling Skype clients, and this library still works on the Skype client that installs through Ubuntu 11.04's Apt repository, so I wrote a small bridge library that uses WebSockets as a transport, and started building a chat bot in NodeJS. Behold, my creation is alive!
Skypekit is a highly proprietary SDK for Skype third party applications. It is non-free, and non-redistributable, but waaayy more up-to-date and deployable than Skype + Skype4Py from what I can tell. I detailed my experience setting up Skypekit with Damonbot in this repo, if you wish to go this route.
Skype4Py appears to be a fairly obsolete / deprecated library. It definitely does not work on the latest Skype client in OSX, and it hasn't been tested in Windows. However, it appears to (mostly) work on Skype 188.8.131.52 as installed through Ubuntu 11.04's Apt repository.
Skype is obviously not a great target platform for fun side-projects, and Skype4Py's days as a functional library are almost certainly numbered. Using WebSockets as a transport mechanism over suitable "bridge" libraries that adapt the bot to various chat platforms should, in theory, allow the bot to be built in a platform agnostic way. It is my hope that even as Skype4Py dissolves into oblivion, or as my company abandon's Skype as a communication platform (oh please, let it be so!), that DamonBot will be transferred to new communication platforms with little effort and no modification of core functionality.