I just stumbled on your post, and it is very interesting, specially the streak thing. I think it’s great that there are more people writing about this topic. I’ve become a huge fan of time tracking and analysis.

I’ve written a small app to help tracking one’s habits and goals, it’s at http://routinetap.com.
If you have the time let me know if it suits your needs, I’m currently working hard to improve it and everyone’s feedback is appreciated!

Thanks!