1) I would just run them all to durotar and level them together there. I think it would be more time-efficient
2) In general, dungeon leveling is a bit slower than questing. With multiboxing, though, I think it's a bit quicker, since a lot of the quests are a pain to do for several characters, and so you would either skip a lot of quests, or grind a lot anyway. I would expect a couple more days than for a regular character. Another Good thing about this dungeon strategy is that you won't have any problems gearing all your characters.
3) If you can handle those classes at once, it's a good setup. But as this is your first time multiboxing, I would advise something more streamlined. I've seem 5x druid many times, for example.
4) If you are going for AoE, I would make that 3 mage instead. Although, you might get aggro problems, since warriors are not amazing with AoE tanking.
Just my opinions on it, take it with a grain of salt please

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