I've passed 5 hours on Tiny Tower, so I'm considering it beaten in liu of an obvious 'win' status. The only one I can think of really is getting all of the achievements, and that to me feels like more of a :C: status.
Play is slowing down a little now. Things are getting really rather expensive to build and my income isn't quite matching the increase. But I suppose that's a big part of the game, keeping you playing for longer. And more likely to buy TowerBux to speed things up. That sounds a bit cynical, but it is a Freemium game and so it's designed to get its hooks into you and get you to buy lots of little bits of stuff. I don't mind though, I have other things to play too, and this is good for bathroom breaks at work.
I've given it 5/5 stars because it is rather good. I might downgrade it to a 4 later if the cost of new floors keeps rising to ridiculous levels, but for now, I'm still having fun, and the things my Bitizens post on 'Bitbook' are still totally funny.