I have decided to start sharing some of my personal projects with the hope that others can extend them in cool and interesting ways.
Take a look at the first one here: https://github.com/maxabrams/PiTweeter
I have synced a copy of a basic python script that, when ran on the Raspberry Pi with your keys, it will tweet the CPU temp, CPU usage, free disk space, and free RAM! Combined with a cron job, this can programmatically check-in as desired.
This is pretty basic, but can easily be extended to tweet anything you want from the Pi.
As a warning, try not to post too many boring tweets - you may start losing followers!