I was jailbroken exactly once - with the jailbreakme.com jailbreak (sorry I've forgotten the name). The thing is, just during the first few seconds of booting, there were a few flashing pixels and IT MADE ME CRAZY that my wonderful user experience was somehow marred. I want to know that my user experience is perfectly and lovingly tuned by Apple's caring craftsmen.

For me it comes down to user experience. I came from a Windows Mobile phone. I had every software that you can imaging and it modded to perfection. The thing is - the user experience was just crap.

When I use my iPhone or iPad, I want to know that it is perfect, and while yeah, it annoyed me at first that I couldn't do stuff that I could on my WinMo phone, the experience and smoothness was just amazing! Since then, with iOS 4.2 and apps like GoodReader and AirVideo, I really have nothing more to complain about.

(this is a reprint from an email I sent to another guy at another blog)

I was jailbroken on both my earlier 3G iPhone and my WiFi iPad. Right now, I have the iPhone 4 (stock) and I just upgraded the iPad from JB 3.2.1 to iOS 4.2.1. I'll probably leave it at is for a while, but I really miss SB settings and being able to use the iPhone as a WiFi hotspot.

Cheers,

I have yet to come across anything I have to do on the iPad I can't do already with iOS.

I'm not jailbroken because there isn't one available yet for iOS 4.2

JB my iPhone 3GS via jailbeakme.com, just to see how it worked. It was a great experience for me, and made my 3GS more customizable for. I recently JB my iPhone 4 using Limera1n, so I could use the MyWi application that I downloaded from Cydia to connect my iPad to for data usage. This works great, and saves me from having to use one of AT&T's iPad data plans..... Can't JB my iPad at the moment, as I am now running iOS 4.2.1, which is only jailbeakable via tethering at this time, and I'd rather not do it that way.....

Because there is no good jailbreak for 4.2.1 yet.

I've yet to read of a must-have app which would make me want to jailbreak.
The iPad's not prefect but it sure gets a lot of things right as is.

Plus it's only a few months to the next version.....