This is more of a knowledge expansion endeavor rather than career endeavor. Something to tinker with on the side was the appeal of the Ubuntu'd Chromebook in a threat here last week.
As far as learning and reversing goes, it has often been helpful to see how something is working while also attempting to make it work for me.
You should still be able to learn quite a bit with just the Chromebook. After reading the article, I'm thinking about getting one myself so I can get back into learning web development again.
Not quite yet. I usually wait until the semester is in full swing before I make purchases. Both for time and money's sake.
That will be the one I more than likely go with. I was worried about 2GB of RAM coming from a Windows background, 2GB isnt anything. But apparently it runs fine in Ubuntu.
That being said, I don't think the $200 Chromebook is going to cut it. Eventually he's going to want to run a Windows VM.