Someday I will learn not to type a long response over the course of two days, only to see it vanish when I hit 'reply!'
I have worked for my friend before and I know that some people find her difficult to work for. She has a very methodical, strategic way of looking at things. If she asks you to make a recommendation, you need to demonstrate that you have thoroughly researched X and the alternatives to X that you discarded for reasons A and B.
I find that it is easy to give her what she is looking for - once you know that you basically need to type up all your notes and thought process into readable English. I wouldn't say that it is micromanagement, exactly - she will not question the decision you made as long as she is confident that *you* questioned it.
She's also very introverted and perhaps seems a bit distant to people because of it. She really cares very, very deeply about people, to an extent that would surprise anyone who watches her daily social interactions. Like if an employee's house burned down, she would let them move into her house, that kind of thing.
She'll never blindside you with a last minute request. Everything is planned and ordered. She's probably the opposite of your boss

Is your boss the kind of person who would give a TEDx talk and talk about it as if he had given a TED talk? He reminds me of someone I know who did that...
I can't believe he had you pick out annual goals based on someone else's strategic initiatives that you'd had two seconds to process. Way to go! I hate those kinds of exercises too, especially when the pointlessness is just driven home by the fact that none of you had any time to put much thought into this. I can't believe he thinks he is a good manager!
How is your foot, btw? I took my first walk in about a month yesterday and it was great.
When you look at jobs, are you looking at *all* jobs, or just stuff in your field? If something outside of your field excites you when nothing related to what you currently do does... that seems like an indication of something, although I am not sure what.