I broke 3 ten gallons before I got the hang of the technique.
I used a drill press, which should have been more "idiot proof".
Here is what I learned.
The bit must be sharp.. Especially if you are buying the cheap ebay diamond bits.
The tank will have a tendency to move/rack as you drill it.
Go very very slow, very light pressure.
As others said, the bigger tanks with thicker glass are actually easier to drill.
Of course, use something like plumber's putty to make a little pond of water around the area you are drilling to cool the bit as you drill (you probably already knew that).
Now as far as long term, I had one problem with breaking a 20 long after it was drilled.
I put the bulkhead in, was plumbing it, I glued some PVC wrong, noticed a few seconds later and tried to pull the PVC off.. The glass broke, but I was pulling hard.
So just be careful.. I have many drilled ten gallons in my fish room.. Once they are drilled and plumbed, no problem, but obviously you shouldn't be bumping into them, etc.