We use Mediawiki. Tracks revisions, lets you rollback, let's you make comments, let's you provide reasons for changes, gives you easy diffs...you can do a private wiki for specific project, or projects. It's free, open source and extensible, the data is portable, easy to move from one SQL to another.
1. When I feel collaboration from my team. The time of day is irrelevant. With a good team, you should always feel "in the zone". Sometimes people begin to drift, if you're a good manager...you know when this starts to happen, and you pull them back together and refocus. Losing focus, and allowing that loss of focus to continue is a bad thing.
2. I don't. Double Cluepon is a startup, not everyone is paid. Sometimes you do work with some people when you can, but you balance it out so something is always getting done. Flexibility is always key, but again..you have to keep yourself focused.
3. We've had some drama in the past. We nip that shit in the bud. Drama, power basing, political bs...we show it the door. We don't need it, actively remove it. Better to remove one, than lose all.
4. As the Production Director and the CEO in a company that makes games, I balance it as best I can. I actually love all aspects, from art to the infrastructure and code. Really, when you're a chief, you have to be a generalist, not a specialist.
5. ALL. THE. TIME. We also hire people who are local. Telecommute is a buzzword in some respects; there is no substitute for face time.
6. It entirely depends on the job. We're in games, sometimes I design away from people, away from my computer. Other times, such as Game Design meetings, I work with others. It ultimately comes down to an amalgamation of what I said above: you do some stuff when you can, do fill in the other time with stuff that still needs doing.
Book it, done.