I'm currently using the independence exploit on my PS2, and setup the exploit for my friends japanese PS2 so he could use cogswap loader to play american games. I used a ARMax pen drive and it was very easy. I spent several weeks reading up on xbox softmodding before I was comfortable doing it, but only a couple days on the PS2 exploit, but perhaps it's because of my newfound experience.
If you're looking for functionality of an Xbox though, you will not find it. The only dashboard-ish applications don't look so great, and HDLoader/Advanced are only compatible with a limited number of games, so it's hardly practical to backup your games because of all the patching you will have to mess with.
The Xbox community is very "lucky" and I somewhat doubt there will be a future console with as much homebrew and backup capability as the Xbox, with or without modchip.