The other thing to consider is that, if you've purchased things off iTunes for use with iPhone, iPod Touch, or even regular iPod, they will (probably) work on the iPad for no additional cost so long as you sync it with your AppStore/iTunes account.

One of the criticisms of Apple is that once you've paid into Apple products, you're stuck because the stuff just isn't portable to other, non-Apple, platforms. For those that have spent a lot of money on music and apps, that can be a significant problem that raises some anti-competition concerns.

On the whole, I think you and he will probably be more satisfied with the iPad and it's demonstrated success rather than waiting and hoping for improvement in a product that, right now, is clearly inferior.

EDIT: you may also want to consider an iPhone or Sprint's EVO, since either one is better for all tasks you anticipate using - except as an ereader which I perceived to be your most common use, and why I didn't include it in my original post. Sprint, btw, is practically giving away EVOs. My friend just got a family Simply Everything, EVO, and other phone for his wife for around $60 for phones and $100/mo ongoing (after corporate discount) AND they credited his account for the contract termination with his previous carrier (your experience may vary).