You're making the mistake of judging the idea too much and forgetting that Drew Houston went to MIT, and had worked as a tech lead at a company. That already puts him in the top 10% of applicants, regardless of his idea.
I guess so. I, on the other hand went to a state school and my work experience is working on fairly straightforward line of business applications. I am not so much criticizing Dropbox as much as I'm making fun of my own lack of vision.
when in doubt, ask for what you want. that's what all the unqualified people are doing, so you might as well do it too.
the most uncommon and valuable skill in the world is for a smart person to willingly put themselves in a position where they could easily fail, or be ridiculed. dumb people do this all the time. this is an advantage to being dumb. you have no ego to lose. nor much of anything else.
that is the cross-section of intelligence and success. just look in the mirror for an example.
and for what it's worth, if you think dropbox is a tepid idea, just consider slack. enterprise irc with history and attachments. worth billions. there's more to it than just a cool idea. the example i always use is: i've got a great idea. let's build a time machine. it'll be great!