Reasons to Jailbreak:
Access to T-Mobile GSM Network
The biggest problem with the iPhone is not the "death grip" that blocks your mobile signal -- it's AT&T. AT&T has exclusive rights over the iPhone until at least 2012, and with all of the network's problems -- mostly related to its tendency to drop calls -- many are justifiably wary of purchasing a phone tied to a problematic network. But the latest jailbreak gives users access to T-Mobile's GSM network, which works overseas and may be more robust in your area.
Cool Jailbroken iPhone Apps
Apple's legit App Store has many cool offerings, but jailbroken iPhones have a wide array of banned creative and quirky apps. Access to Cydia -- the hub of "illegitimate" apps -- is a huge motivation for jailbreaking your iPhone. There are many lists of great jailbreak apps to check out -- here are a few standouts:
MyWi: Turns phones into mobile hotspots
Intelliscreen: Puts e-mail and calendars on the home screen
MxTube: Download YouTube videos onto your phone for offline viewing
My3G: Allows for previously Wi-Fi-only processes to run on 3G, like HD YouTube videos
PDANet: Share Internet connection
Fast and Easy
One of the best parts about jailbreakme is how quick and easy it is to open up your iPhone. No need to download software onto your desktop or hunt for updates that dodge jailbreak-killing iTunes updates -- by using the Web browser, the whole process takes less than a few minutes over a Wi-Fi connection. Still, you can expect Apple to release a patch that will shut jailbreakme down at least temporarily.
Fully Reversible
If you're scared of the consequences of jailbreaking your iPhone -- or simply don't like the experience -- jailbreakme is fully reversible. According to jailbreakme.com, "If you ever decide that you want to remove your jailbreak, just connect your device to your computer, sync, and then press Restore in iTunes." Beware: if you upgrade past iOS version 4.0.1, there may be some unknown outcomes.
FaceTime Video Chat over 3G
FaceTime video chat is a nifty new feature of the iPhone 4, but it only works over a Wi-Fi network, which may be difficult to find in many situations. Jailbreaking the iPhone 4 allows for FaceTime video chat over a 3G connection. The results are less-than-pretty, but it's more convenient and won't be interrupted if you have a good signal or walk out of Wi-Fi range.
Access to forbidden apps and services: The App Stort has a remarkable collection of apps and Apple's slogan, "There's an app for that," is close to the mark. But it's not entirely true. There are things Apple won't let you do with your iPhone via apps sold at the App Store.
For example, although Steve Jobs can project every element of the iPhone's interface on a big screen, you can't. Video output on the iPhone is limited, by default, to select apps. This can be done, however, with a third-party app found via the Cydia app. (Cydia is an application installed when you jailbreak your iOS device that provides access to third-party applications not submitted to/approved by Apple).
Or this: AT&T charges $20 a month for wired tethering--using your iPhone as a modem for your attached computer. For that $20 a month, AT&T provides no extra data, it's simply granting you the privilege to use the iPhone in this way. Cydia offers a handful of apps that provide this functionality for no additional charge.
Jailbreaking also lets you customize the iPhone's interface in ways not allowed by Apple. You can, for example, apply themes that change the iPhone's wallpaper as well as its icons. You can also enable video recording on older phones like the iPhone 3G that don't natively support it. And, with the installation of SSH, you have the ability to access every part of the iPhone--as you can with your Mac--rather than just those specific areas allowed by Apple.