Some thoughts:

It's a little odd that it wouldn't allow you to install Chrome extensions from outside of the market

The external harddrives probably DID work, and would show him images if he used something that required browsing for them

As much as I hate to admit it, he's right about iTunes. Who with an iP{{o,a}d,oop} would be able to use this thing alone as primary pc?

How do floating pop up type windows work? I.e. clicking the pop out button on google chat, or hulu

For a web-centric machine, those 3g plans seem a little towards the expensive side, with pretty low data allowances. But on the other hand, I don't really know how many bytes "regular browsing" accumulates in a month.