If you need to know about jailbreaking, I'm the guy to call, I've jailbroken my iPhone, iPod touch, and others iPod touches too many times to call
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But yes, jailbreak it for the love of god, it adds 300% more fun to the iPod, including skins (which is a big one), and ROMS, which are quite fun too!
I am also active at iPodtouchFans.com being the 2,094th member out of about 345,000, so I can say I'm an early bird there
They now have skype straight from the AppStore for the iPod touch, so get that if you want to call
As for jailbreaking, use Redsn0w.com