I dare say that TT could give Guild a run in a shoot out with a proper crew. With Misaki's redonkulous charge range and rules, she will get to charge whatever she wants. She doesn't do mad damage but with stalking bisento and recalled training she will hit hard for one turn. Without knowing what else was in the TT crew its hard to say what you did wrong. But as mentioned previously, if you can kill the upgrade holder, blot the skies will be gone. Hiding in melee won't help you against them either.
Your crew seems to have hampered you a bit as well. Lawyers and executioner are less than optimal from what I've gathered. I believe riflemen actually outrange TT archers by 2".
Also, Misaki is hardly game breaking. She's an assassin. she should be good at that. She will die to range attacks, of which guild has plenty.