Should I jailbreak my iPad?

Solution 1:

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.

Solution 2:

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• Backgrounder allows a (now outdated) type of multitasking.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!