Is there a way to read the contents of a static data directory or interact with that data in any way from within the code of an application?
Edit: Please excuse me if it wasn't clear at first, I mean getting a list of the files in that directory, not reading the data in them.
No. Files marked as static in app.yaml are not available to your application; they're served from separate servers.
If you just need to list them, you could build a list as part of your deploy process. If you need to actually read them, you'll need to include a second copy in your application directory (although the "copy" can be just a symlink; appcfg.py will follow symlinks and upload them.)