Ideally, client side encryption might be a good solution for this. From what I've seen, there isn't a public API to work with skydive. Even some open-source efforts are mostly outdated by now. Maybe that could be something worth looking?
http://ycombinator.com/newswelcome.html : ("A crap link is one that's only superficially interesting. Stories on HN don't have to be about hacking, because good hackers aren't only interested in hacking, but they do have to be deeply interesting.")
damn you [developer of this], had this idea pending for the longest time. yeah, I know this crowd knows this line too much.
Anyway, my approach would be different by a single feature: movie sync. I've already watched many of the movies listed, and would be great to give you my imdb rating public url and you filtering those out. You could even implement a basic recommendation system using my ratings to give best matches.
mind telling more about your experience on this?
how far would you say "getting out of your comfort zone" did you reach?
how did programming affected your life (seems like you meant you spent too much time doing so before getting to that... how was it?)