Hey Ruddy
As someone who went through hard times over the past 9 months, almost everything you mention either happened to me or I had
very similar experiences. I had a couple of emotional 'distresses' over my hairline, the likes of which I had never gone through before, and haven't had ever since I started buzzing, and now that I'm truly shaved, all I can see is positives for the future (if only my newly shaved scalp would hurry up and tan

)
You've accepted the fact that you'll be shaving your head eventually anyways. I'm not going to BS you and say that shaving it off will magically make your problems go away, but I can say, from what I went through, that the best solution to this problem is not to dwell on it (or try to regrow it), and the best way not to dwell on it is to get rid of the source - which is your hair.
Again, I can only speak from what I've experienced, and what I've experienced is that, at the
very least, I should have buzzed my hair down 9 months ago when it all started going downhill for me, rather than get caught up in the spiral of Rogaine and Propecia. Because the minute I buzzed it, everything that bothered me about my hair disappeared. I realized that I wasted the latter half of last summer and most of my current junior year of college kicking myself over this. And then my bro convinced me to do what he did - shave it off. And I can't believe I waited so long. It's a common feeling, and chances are you'd feel the same way.
And my head isn't perfectly shaped either - it's slightly oversized for my 5'6'' frame. But it's
my head, and I wouldn't have it any other way.
I say, you should buzz or shave your head, get some stylin' and
sly clothes, and go meet your fellow balding friends. Once they see how freakin' awesome you look, they might be convinced to do the same. And you guys can go hit up the nearest bar and show them what a couple of
sly bald guys can do

Don't let hairloss be the crutch that slows you down. Let it be the thing that speeds up your transformation into the coolest guy around. When I started college, I wanted that cliche transformation into the "new me", but it never happened... until now. I wish I didn't wait so long to do it.
Give it a try, go sly! You just might be surprised.