Michele~

In a part of your post I believe that you were clear that you were not talking about all men. Because of that I didn't receive all of your post as generalizing your meaning as "all" men. Although, I can understand how some are sensitive to one gender generalizing the other, therefore assumptions are created.

Far be it for me to answer these questions FOR the men, (as I'm not of the gender, myself..lol), but I think some of your questions apply to both sexes, as a person's trait in general.

I think GrayNess did a pretty good job on answering most. And Tim finished where Gray left off..lol.

I think most of your questions regard mostly upon the issues your sweetie has, which seem to be insecurity of self and possibly trust issues? Not sure.
I can personally relate to some of your questions as I used to wonder those very same things throughout my first marriage.

The ex was extremely jealous, (thus very insecure), and throughout the 10 years we were together he would find one reason after the next to use as a means of justifying why MY friends (first all the male ones, then the female), and reasons why I shouldn't do this,or the other...all were not good for "me", (If only I knew then, at that time, what I learned later on.....).
I never gave him reason to be jealous. I "behaved" accordingly for the sake of our relationship. But after years had passed, and I eventually ended up without anything I could call my own, including my own friends, (he "allowed" me to have my family and his friends in my life without his judgement casted....(how thoughtful of him ...lol).

Granted, jealousy is a natural emotion. But when it conducts one's behavior, then in my opinion, it transforms into possessiveness, which is very harmful.

Apparently, Jerry may feel threatened by you seeking self-improvement for fear that once you have obtained the health that you are seeking for yourself, that (because of his insecurity), you might not view him the same way as before. Yet, he has the tendency to hurt your feelings, (intended or not...it still hurts, regardless), by mentioning to you that you aren't the "model material", (I know how this can hurt..happened to me, as well, and it does leave deep, lasting emotional scars).
This behavior of his, (the push in one direction, pull in the other...thus his indecisiveness which stems from his insecurity), isn't intentional. I don't think he's even aware that he does it...or, so it would seem.
Perhaps, you can encourage him into counselling together? Guide him to seeking answers to his own issues. Lord knows, you cannot fixie FOR him, and unfortunately, you will remain the target of his issues so long as he doesn't attend to them himself.

One should not have to continue to make sacrifices for the sake of the other, (especially due to insecurities), JUST to maintain peace between the two. I made that mistake, and lost alot in the process, including my own self.

There has to be a medium found between the two of you...something that is reasonable and you both can accept without much sacrifice for either of you. "The happy Compromise"
So long as he is not willing to meet you halfway, and continue to cast all the responsibility upon you to do the changing (sacrificing) to meet his needs, then you very well may end up in some serious trouble later on. I'd hate for that to happen for you...for either of you.

I hope this works out for the both of you. I know what he means to you.

All the best......
(Hope this helped some)

Shangrala