The only problem is putting a new drive in there. To be honest, that is the only thing I haven't personally done. Modding it to play copied games is very simple. (even Freak can do that) Once you have a new HD in there and you have a game you want to copy, it's a matter of pressing a few buttons on the controller...very easy. I've read a new HD swap isn't that hard, it's just I haven't done it personally since all the mods I've done for folks just play games off DVDR.
Now, if you're a little tech savy, you can just make copies of the games onto DVDR. (DVD writer if you don't have one is roughly $50-$60 nowdays) I say tech savy because you end up putting the xbox on your network and then ripping the game disc across your network. Work involved is hooking up your xbox to your router and loading a little piece of software on your computer. Computer DVD drives cannot read the discs, so it has to be done in the XBOX.
Going with the copy method, you're looking at 10 minutes to rip the disc to your computer, 10 minutes to create an ISO from the files, and 10 minutes to burn (very rough estimates, probably on the long side). Again, this might sound complex, but it's really not and ends up being just a few mouse clicks.
If you are going this route, I suggest you buy a used XBOX. New units on the shelves a bit different and could cause problems. From there, let me (or one or two other members here) know that you need it modded. I can set it up without a new HD in 10 minutes.
You got a DVD writer and router? Think you'd be comfy hooking it up to your network? It's not all that hard and I could walk you through copying games by phone given that you have all the parts.
Again, I do not condone piracy or theft. I just read a lot and help out degenerate friends.
