Robert,
I can't know all you are experiencing but a lot of what you have said here I have felt too. I have written extensively here about the experiences I've had so I won't repeat them now but I will tell you I have experienced more emotional pain this past year than I ever thought I could handle.
As far as rushing your transition just because you want to realize the maximim benefit from HRT due to your age, realize that everyone is different. Some mature early, some late. Some have the genetics that would allow for a very successful transition at almost any age, some not at any age once testosterone has had its effect. Only an experienced doctor can give you a reasonably accurate assessment of what you can expect. I was 53 when I saw one and he told me, "I've been doing this a long time and I can tell who will do well and who won't. You'll do very well." So don't let the age issue be your sole motivation to transition.
Your best bet is to first determine if transitioning is the right choice for you. If you come from a less than accepting family like mine I suggest you go as far as you can without disclosing anything to them. That way if you find it's not right for you no permanent damage will have been done. I took my therapist's advice and fully disclosed my intentions to transition and I lost my wife, my son and now it seems my daughter, not to mention my brother, mother and a couple of sisters. It's like I have the plague. And I'm not transitioning. So be careful about disclosure.
The more you know the better chances you have of making the right decision. Besides the sites mentioned above, here are some others that might help you:
