Secondly, when building a simple fun tool to be used on websites, is a four-image team bio with MIT written in capital letters all over it necessary?

Putting images on a web page is easy, so we see images everywhere on the Web. If it were also easy, we would expect to see good file upload widgets everywhere. Good file upload widgets are not everywhere. From this, we can conclude that it is still an open problem.

Because we're tired of not being able to live entirely online, and this is one small step in that direction

I think the point is that is will support pulling files from any service you use to store them - dropbox, facebook, your computer, skydrive, etc. It's much more than a pretty file upload UI, and the fact that it looks that simple is actually its greatest achievement.

Why not? This isn't necessarily all they're doing with their time and (assumed) talent.

They've got this MBA dude who's calling himself a hustler so they'll be alright :D

The Brass Rat messes with those guys' minds.