I don't have an iPad. My youngest son (teenager) got an iPad 2 for Christmas as well. Even with an OtterBox I don't think he'd ever bring it with him in a park. Too much bulk and not any need for it. He also has an iPhone 3GS.
However, bringing some sort of laptop, tablet, etc. to access email on a vacation for work purposes is a must for my DH. There's some types of work that even when you're on vacation you still need to be available to answer questions if the need should arrise. Also, I've known people who needed to attend meetings via computer while on vacation. Is it fun? No.
But it's also time you can charge to the company and be compensated for if it should occur. Just sayin', it *does* happen and not necessarily for the people in this world who looooove to work because my old man definitely lives by: Work to live, not live to work.