A couple of friends of mine and I have agreed to go through the first few lectures of this still super-relevant and foundational machine learning class:

http://openclassroom.stanford.edu/MainFolder/CoursePage.php?...

Why not join us with Swift implementations of some of the discussed algorithms? Simultaneously, you could also experiment with some of the cool, puristic functional programming libraries recently coming up for Swift. Check out awesome-swift:

https://github.com/matteocrippa/awesome-swift

In any case server side application of machine-learning has its drawbacks in terms of privacy, reality of losing internet connectivity, etc.

Hit me up on twitter or github if you are interested.

Have fun and happy holidays (don't forget to relax) :)