Should I jailbreak my iPad?

I just got an iPad a couple of weeks ago. I had a co-worker pull out his iPad out and immediately start talking about jailbreaking it. I have no fear of doing it, but I do realize that sometimes going beyond what the manufacturer intended ends up making your device less stable.

What I'd like to get from you guys is your favorite pros and cons for jailbreaking an iPad specifically. Will I have upgrade issues when they ship iOS 4 for it? Will it crash? What are the killer features if I do go for it?

Pros:

  • ability to install apps not found in Apple's App Store
  • ability to customize the OS, UI, etc. to remove minor annoyances and trick out your iPad

Cons:

  • you will definitely be unable to upgrade to new versions of the OS without having to re-jailbreak
  • your iPad may be less stable
  • you can't bring your iPad in for warranty service without undoing the jailbreak
  • time & energy: researching and performing the jailbreak, finding/installing non-App Store apps, keeping abreast of the latest jailbreak status in the face of updates, etc.

I've gone both ways depending on my needs -- my iPhone is jailbroken, my iPad is not.

In addition to pinko's list, here are some specific apps.

  • Backgrounder allows a (now outdated) type of multitasking. It was ok on iPhone 3G, but with the iPad's more powerful processor, it may be more stable.

  • MyWi allows you to tether for free if you've got the 3G iPad ($9.99 for the app). But you said you did that with a rooted G1 already.

  • For me, it's cool to have access to the filesystem. Utilities like Mobile Terminal, OpenSSH, and iFile are of specific interest to me just for my own nerdish pleasures lol.

Hope this helps!

To add to this list:

  • Browser Changer removes the need to use Safari for anything
  • WinterBoard allows theming (though many skins aren't iPad-compatible)
  • SBSettings allows you to hide icons and ReNamer lets you rename them
  • snes4iphone, nes4iphone and gpSPhone are basically perfect emulators for SNES, NES, and GBA, respectively
  • psx4all plays many (but not all) PlayStation games perfectly (though it is unusable if you have WiFi off thanks to its crappy implementation of AdMob)
  • n64iphone doesn't work with many games yet (or is unaplayably slow), but it's nice to see the future of iPad emulation

The biggest con to me is that it is possible that one day you'll go to use your iPad and it won't work anymore. You would probably be able to fix it, but would it be worth the hassle?