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Multi-tasking (proper, apps running in the background multitasking) is one of the biggest reasons to jailbreak. Also the ability to run apps that Apple doesn't want in the iTunes store (like wifi syncing with iTunes), tethering (for 3G iPads and iPhones) without having to pay an extra $30/mo, the ability to run iphone/ipod apps full-screen (doesn't work well for every iphone/ipod app, but works great with the facebook app), and much more. Essentially it lets you use your iPad the way you want to, not the way Apple wants you to.
Once jailbroken, there's no need to unjailbreak. iTunes store apps continue to work just fine. Jailbreaking only adds additional features. However if you do ever want to un-jailbreak, you can simply restore an older backup, or reset the iPad to factory, or install an OS upgrade that hasn't yet been jailbroken. If you're worried about warranty support, it's easy enough to take a backup and then reset your iPad to factory before taking it into the store.
Note: I don't have an iPad, but I've jailbroken my iPhone in the past. I upgraded to iOS 4 which undid the jailbreak, so I'm waiting for the new Spirit-style jailbreak to ship (should be right after Apple ships 4.0.1).
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