Jailbreaking screws up nothing with iTunes or the store.
You get an update notice via iTunes, decline it. Jailbroken forever, or until the next version of the firmware is cracked IF you choose to keep on the Apple supplied patches, you will need to wait until a jailbreak comes available for it. Jailbreaking actually got the bug fixed (pdf) this last round long before Apple got around to it.
I find all my iOS devices nice to use in stock mode, but Jailbreaking under Cydia certainly give you customization options you simply will likely never have under the stock iOS. In some cases, stuff like tethering is only possible on jailbroken devices if your provider does not support it on the iOS devices. Sadly, Apple locks them down pretty good out of the box. They are usable in stock forum, but it's akin to buying a shiny new car that you cannot open the hood on, can't tinker with the motor if you are a gearhead. Jailbreak/Cydia allows that.
Both Android and iOS are very nice to use, but I have had a far more stable and crash free experience on the apple products than I have on Android. Rarely hit apps on iOS devices that crash, where as the wide spectrum of hardware (and differing Android OS versions) Android runs on can sometimes be a bit sticky. Virtually all of the major handset makers customize their interfaces on Android, making a "universal" experience that iOS offers a little harder to come by.
That being said - I hate the iPhone as a phone, for voice calls. It certainly is usable, but I was a BB user for many years and I've used far, far better handsets when it comes down to sheer voicecall quality. Thankfully I use it more of a SMS/text and email device far more often than for a voice phone. I'm not an Apple fanboy in the least, but I do like their consumer goods - but Android's market share is only going to increase, and Android devices are more than usable and improving quickly.
