If you've already started drilling, you're probably pretty much committed to this course of action at this point. May as well give it a go as the worst case is that you need a new caliper which you may need at this point anyway.
As mentioned above the bottom of the bleeder screw is of a smaller size then the threaded portion, so stop occasionally and look down the hole you're drilling. Stop when you see any sign of breaking through the bottom. Now that you have depth set, work the diameter up until the bottom falls out or is just about to. Just when you think you can probably get away with one size larger, STOP! lol. If you see ANY sign of the threads along the sides of your hole, stop because you've gone too far. At this point the threads are just a thin shell along the inside of the hole and with a little determination should be extractable as mentioned above.
At worst, a replacement caliper shouldn't be too hard to come by around this place.
For a replacement bleeder you should be able to get a speedbleeder:
![](http://www.speedbleeder.com/images/sbani.gif)
best of luck!
mystic_1