In the event of a Jailbreak, Which I'm considering, What website/s should I trust? And do the risks out weigh the benefits?
You shouldn't be too worried about it. I've jailbroken lots of iPhones and iPods and nothing has gone horribly wrong. Most if not everything is reversible so don't worry. As for places to go, redmondpie.com has a good guide, lifehacker.com also has one. Most of the things that you find on the Internet are good as long as they aren't asking you to pay for it. blog.iphone-dev.org is the official dev-team site so that's always a good starting place.