When playing exhibition games, you can coach both teams. I've tried it, but didn't really like it since it was difficult to keep focused on both teams at the same time and also difficult not to subconsciously favor one team or the other.
I don't believe you can coach both teams when playing your association, though, since while you'd be able to coach the team for the head coach you logged in with but the game doesn't allow you to change the coaching icon from AI control for the opposing team.
Simming the h-2-h games seems the best since that way you aren't favoring either team. If you want to watch the game, you still can, just click on the coaching icon before the game to make both teams be AI controlled.
And you still can play out other games so you get a good feel for the players of the four teams (and get to enjoy the courts).
Glad to see the new dynasty, Tim...nice concept.
The recruiting conflicts should be an interesting (and possibly challenging) twist.
Coach Jackson needs to quit spending money on reports and trips so he will have enough money to "buy" some players.