I've drilled about 15 tanks or so, from 5g up to 75g. The smaller tanks are MUCH harder. If you can drill a 10g, you can drill a larger tank.
Go slow, let the drills weight do the work. Speed doesn't really matter all that much if you can keep the drill/bit from wobbling and don't have much down force. Cordless drills tend to wobble a bit more, but that's all I've ever used. I usually start pretty slow and speed up as I go.
Drill the tank from the correct way, which means you shouldn't always start on the outside of the tank. When drilling a tank, when the drill bit goes through the last little piece of glass, it will chip a bit. If this chip is big, the gasket won't seal well. This matters more with smaller gaskets/bulkheads, but is applicable to them all. Start drilling the hole from whichever side the gasket will be on. If you are drilling from the inside of the tank out, there's no need for a water damn, just fill the tank with 1/2" of water. Or, set the tank on it's side and fill it up until the water runs over the 3/8" plastic edge.
Build a guide to start the hole perfectly. With a guide, the bit won't "walk" and you will have a perfect hole in the glass where you start drilling. I take a 6"x6" piece of 3/4" plywood and cut a "V" shape into one end. Clamp or tape (electrical tape doesn't leave adhesive behind) this down to the tank. Press the bit against the V when drilling (at least until you get the hole started).