To jailbreak or not to jailbreak? If you'd like to be able to run apps in the background and do other cool tricks like sharing your 3G connection with other devices and fooling the system into thinking you're connected to Wi-Fi instead of 3G, then yes, you should.
Jailbreaking is even more compelling when you consider how easy it is to do. The new Spirit jailbreak makes the procedure a one-click process the only catch is you need to be running a version of iTunes earlier than 9.2. If you've already updated iTunes to the latest version, you'll need to uninstall it and then install iTunes 9.1 or 9.0 you'll be able to find direct links for these versions easily with a Google search.
Before you get started on the jailbreak, do a full backup of your iPad through iTunes just in case anything goes awry. If the jailbreak doesn't complete successfully for whatever reason, you'll be able to get your iPad working again by doing a restore in iTunes this will return your iPad to factory settings, and you can then restore all of your data with your backup file.
After you download Spirit, unzip the file and run the executable. The software itself is refreshingly straightforward, with just a simple 'Jailbreak' button. Plug your iPad in, then click 'Jailbreak'. Once it says 'Jailbreak Complete!', your iPad will restart, and you'll have a new Cydia icon on your home screen. Cydia is basically the jailbreak version of the App Store, and this is where you'll find all of the 'verboten' apps that Apple doesn't permit in the App Store.
Apps you should download
Just don't go crazy downloading every app you see there. Most of the apps on Cydia were written for iPhones, and only a limited subset of these will work properly on the iPad. Backgrounder is probably the most popular of these, as it adds multi-tasking capability ahead of the iOS 4 update. You'll need to manually enable each app that you want to run in the background, which you do by pressing and holding down the home button while that app is open.
If you've got a 3G iPad, you'll be able to share your data connection with other Wi-Fi-enabled devices over a wireless network using the handy MyWi app. It doesn't come cheap (at US$19.99) but it's well worth it for the freedom you get to use your 3G data across multiple devices.
If you're on one of the unlimited data plans from Optus or Vodafone, even better.
Another app for the 3G iPad users, 3G Unrestrictor essentially tricks the OS into thinking you're connected to a Wi-Fi network when in reality you're connected over 3G. This is useful for apps that will only work over Wi-Fi (such as Skype) and also for getting around app restrictions like the 20MB download limit in iTunes and App Store and the lower-quality video stream for 3G in YouTube.
If you're not a fan of the distorted pixel-doubled look of iPhone-only apps on your iPad, FullForce does it in a much more elegant way that doesn't stretch out the text and graphics. After you install it, you'll need to enable each iPhone app for FullForce in the main Settings.
Finally, there's Winterboard. A long-time favourite of iPhone users for its customisation capabilities, it's been updated for iPad and changes the look of the lock screen, icons, text, system sounds and more.
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