I JUST drilled my 55 gallon tank, I was pretty nervous.....and it turned out to be incredibly easy. I had my brother poor water over it as I went. Just start at a good angle and hold steady so your not bouncing around, as you get your groove going, turn the drill upright and the rest is just patience. You probably don't have to (you probably should, but I dont want to say you HAVE to if its not really necessary), but I stopped every minute or so to inspect my progress and make sure the bit doesn't get too hot.
I spent $8 on a bit from the big auction site, and you can buy a bulkhead off of any reef supply site that sells in bulk quantities
The bulkheads specs will tell you what size hole saw you need.