You're going to have to be the one that plugs the connector into the bottom of the tablet. The technology can't do that step yet. Otherwise, the rest of the procedure can be left up to the technology...
Sreiously though, if you can help it, don't drain the battery all the way flat. That said, you don't have to be completely anal about self imposing a hard cutoff. If you have a long day once in a while and run her down to the teens, it isn't the end of the world.
Only thing that is really a no-no is to run it flat and store it that way. You really will shorten the batt life if you run it down really low and then store it without at least charging it back up first.