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ISBoxer has a mouse repeating ability but I don't believe it has the ability to give you mouse movement (other than click to move) on more than 1 character. Even if it did server lag is going to result in some serious frustration as the longer you run the more the characters will seperate, even if they start in the exact same position.
ISBoxer gives you full mouse control, not just sending a click, so yes it will let you use mouselook on all screens at once. Otherwise correct: you will not be able to get your characters facing the exact same direction and at the exact same point in the world, without hacks.. and different windows will probably lag at different moments, so even if they did, they wouldn't stay together. The entertainment value, however, is worth it ;)