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I don't teach the stances, as it seems to be preference to me. For example, certain stances are good against others (Chudan is good against Jodan [Water over fire] while Jodan is supposed to be good against Hasso [Fire over Wood]), but it just depends on your skill. I use the chudan a lot because of it's simplicity (chudan means middle, so it's the basic, middle stance), but my favorites are Waki and Hasso, with Waki being preferable for Samurai techniques like Iaido, though Hasso is when I become the most fearsome as a fighter. I honestly thing that the stances are better left up to your own experimentation.
Two bokkens, eh? Fighting one v two is always interesting for me....
*When I see you attempting your diagonal slash, I very quickly step backwards, avoiding the slash - when your blade clears my body, though, I very quickly step forward and stab at the center of your chest with my own bokken, held in my right hand. With your blade still coming upward from your slash, due to the timing of my movement, countering it with your blade would be difficult.*
I'll try to give advice when I can. However, I can't tell you much about starting a fight. xd That's always hard.