Here's my view on Jailbreaking (as someone who is choosing not to do it)...
I just don't enough long-term benefit for the immediate hassle. I completely understand the need to tinker with things. I'm the kind of guy who enjoys going through his music collection just to re-rip old CD's at a higher quality. I also understand the sentiment of the guy who felt like using the device "as is" was like driving a Porsche no faster than 50mph. When I used BlackBerry, I often would try out the "leaked" operating systems to see the latest and greatest on my phone.
But it would one thing if Apple was the type of company that never supported their products. This isn't the case. Apple is actually fairly aggressive about rolling out updates to their operating system, and applying those changes even to devices one or two generations back. And now that we've just gotten a jailbreak for 5.0.1, we're apparently pretty close to a 5.1 official release, which renders the 5.0.1 jailbreak either useless, closes off a lot of the loopholes exploited in that jailbreak, or offers new features in an official release that are better than an old jailbroken version anyway.
It's one thing to hack around with computer or tablet for fun to see if you can make it function better. But this is a phone. It's a device I use for work, and I need it to function like it should when I'm making business and personal calls. There's also the endless possibility for unintended consequences where some aspect of the jailbreaking causes an app or other function not to work properly. Even if that possibility is remote, I just don't want to worry about the stability of my phone.
When you sign up for an Apple device, you pretty much know that you're giving up a lot of customization and freedom in exchange for universality and ease of use. Your phone could ALWAYS work better or do something more, but I prefer to accept it as it is, and it's an exceptional product out of the box.