I am speaking from experience as director and co-director of a large number of tournaments at UCLA. I would prefer not to speak from my experiences in high school, as for as good of a tournament as it was there were some major problems (e.g. using Excel for individual stats, moderators getting through 12 questions in a room half the questions were powered).
1) Describe the timeline to organize your tournament. How many teams, how much food, how many rooms...
The size of our club has prohibited us from running a tournament with over 24 teams. I know that sounds small to a lot of people, but most high school tournaments here get 12-24 teams and college ones get <10. For the past few high school tournaments I have picked a weekend or group of weekends and let the coaches decide which ones would be best for their teams. Because of this and a couple of other issues, we inevitably do 90% of the logistics the week before the tournament.
We reserve 1 room for every 2 teams plus a lecture hall to double as a stats room, then sometimes an additional room in case something happens like we're locked out of a room. We prefer small seminar-style rooms with long tables instead of those with individual chair-and-table sets (especially those bolted to the ground).
We typically give an hour to an hour and a half for lunch. The student union is about a 10 minute walk from the tournament site, and some teams choose to drive to local restaurants. For last June's mirror, someone ordered pizza between the academic and trash mirrors. I don't know how that went.
2) How much time do you need to write "enough" questions? How much do you spend on questions?
The vast majority of our high school tournaments have been from NAQT. At the college level, we try to mirror/packet swap/co-edit. As far as I know we have never run an entirely house-written tournament, although that may be something I'd like to try for high schools this year.
3) How do you outreach to teams to participate in your event?
Stanford set up a (e-mail) mailing list for west coast college teams a couple of years ago, and we followed suit with one for area high school teams. UCI has also set up a similar one for information about their tournaments.
4) How do you train your officials and moderating staff?
Most of our moderators are current or former club members. Almost all members gain experience moderating at club practices. If we feel one of the moderators might be lacking experience, we will sometimes make him/her read multiple packets at practice the week before the tournament.
We do not train our statspeople. Pretty much whoever gets stuck with the job has to learn SQBS on the fly. For ACF Regionals 2005 some of the players moderated during their bye round (a common practice, especially when it's your packet being read) so that I could input all the stats.
5) Do you actually make money off your event?
We have lost money on several events in the past, but for the most part we make money off the events. Our main source of non-CBI funding is the high school tournament(s) we run.
I would like to add two more questions, which I think are relevant to the "troubleshooting" aspect of tournament direction. In the past few years we have had several different problems with checks made out to entities that are not us, and therefore, that we cannot actually get any money from. We have also had complaints from coaches, players, or staff about conduct of players/coaches during games.
7) What is your policy on payment, and how do/would you deal with teams that think they have paid but have given you no way of actually getting the money?
8) Under what circumstances, other than moderator error or equipment malfunction, would you find it advisable or necessary to (a) replay an portion of a match, or the entire match, and (b) suspend a player or coach for a game or the rest of the tournament?