It is not all that difficult to drill a tank. Bulk Reef Supply has some good instructional videos on how to do it.
I think it is worth it - sumps are great for both biological filtration and hiding all your equipment, not to mention adding a lot of additional volume to the tank.
As for where to drill, I couldn't tell you as I have only ran a tank with the bottom drilled, a durso stand pipe, and an overflow.
1 word of caution: If the bottom of the tank is tempered glass (as they often can be) you can't drill it. In that case, you would have to drill the sides. Seems like most folks who drill their own end up going the side route anyway.