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As always, HTBT to truly know, but here are some thoughts to consider:
If you truly felt a warning of the coach was the right thing in the first scenario, perhaps right before the second half began a quiet word with him would have worked. Perhaps something along the lines of, "Coach, there was a lot of commentary from your bench in the first half. We are more than happy to answer your legitimate questions but commentary from the assistant(s) needs to stop. Thanks."
I've also got no problem with you stopping play at a dead ball - or even stopping play if it's at a good place to stop - for a formal warning. I don't use this tactic, but others have effectively. If you are going to use this, though, I'd recommend choosing a time when there is a specific behavior happening to refer to.
In the second scenario, sounds to me like you may have tried too hard to reason with him. Walking him back to the box worked, at that point you've probably heard enough and can say so. You aren't going to "win" that one, so move away. At that point, he earns the T if he continues.
Sounds like a righteous T from your description, it just sounds like you may have tried too hard to reason with him.
Good job on taking care of business there.
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