3 board members, investors choose 1, I choose 2 (myself + 1). Do I choose a under-qualified ally or qualified person with no allegiance?

I'd pick an alley if I were you. If you find a qualified one, all the better. If you're a young company, which it sounds like you are, boards are bullshit. Really doesn't matter until you get into later funding rounds. At that point, you're going to thank yourself that you have a friendly on board.

Timely post: http://www.shareholderssquaretable.com/disqualifying-dissident-nominees/