Hi Jamie and Cindy,
I've lived in California before, and I loved it there. I had a chance to grow my hair out a little bit, pierce my ears, and shave my legs in peace. Oddly, in my case, those things got taken as masculine, in the way that adding a little bit of salt to something sweet adds to the perception of sweetness.
You've described my concerns exactly. The endocrinologist in the town where I live refuses to treat osteoporosis in anyone under 65, and he refuses to give me estrogen without a diagnosis of 'Transsexualität'. My GP (Hausarzt) sympathizes with me, but his solution is to send me to another endocrinologist whose specialty is adult diabetes. This isn't going to work. I need someone who has the authority to allow me access to estrogen and who knows something about gender issues. So currently I am under the care of nobody, apart from a sympathetic Hausarzt, and I've been going in circles trying to obtain hormones for the better part of a year. This has gotten so frustrating that it leads to the occasional panic attack. Osteoporosis! Stuck in boy mode!
In my part of Germany there is a clinic which has been mentioned elsewhere on these boards as particularly problematic (See Fencesitter's posts.). They're sticklers for the very long 'real life test/experience' as a man in a dress, despite my hugely masculine body, deep voice, and dark 5:00 shadow, and they're big on policing 'autogynephiles' and the gender binary.

If I actually transition over the longer run in small steps, that would be great, but trying to 'force' a full, binary transition now to please someone like this would be a huge mistake. Here's a list of things working in my favor and against, respectively, as I see it, holding my inability to get medical help aside:
In my favor:
Despite my age (34) I look somewhat younger, and I apparently have a certain 'energy' about me which gets me described as 'cute'.
A year and a half totally without testosterone has had some softening effect, to the point of where people see me as masculine but not 100% so. Someone 'read' me as an FtM (lol) the other day.
My Adam's Apple is not usually visible.
I am not hugely overweight (though I have to watch out for this since my metabolism isn't all that great right now).
I have begun paying for laser treatments out of my own pocket.
My voice has a certain non-masculine lilt.
My mannerisms are not completely masculine.
I am not hugely athletic or muscle-bound, but no couch potato either.
I have full lips and expressive eyes.
I have a full head of hair.
Apparently, a number of my coworkers don't even recognize me after growing my hair out again, and one visitor commented to me that he looked over toward my office and thought that it had been given to a woman. Apparently people have picked up on something already, and the 'surfer hair' jokes have begun. This is despite never having left boy mode in my life, except for 20 minutes in Thailand and 5 minutes in the bathroom the other day.
I already have a big chunk of my 'medical issues' dealt with, through various means. I do not foresee surgery in my future.

I am American, so the German name-change law doesn't affect me. First I do it in the US (easy) and then it propagates to Germany.
I am highly educated and speak calmly even when frustrated, most of the time at least.
I am not the first person in my profession who would be openly trans.
Against me:
I am still 34, and my features have had some time to 'set'. Overall, my facial structure and body are quite masculine--not 100% but maybe 90%.
My chest is pretty flat.
I am over six feet tall, with hands and feet that are not huge but still 'manly'.
I have no access to estrogen.
I have no local support network (yet, working on that).
I have a very thick 5:00 shadow, so it will take quite a while before my 5:00 shadow becomes much less of an issue.
These laser treatments are expensive, as estrogen would be, were I to find some.
I live in a small city so I have to be careful going out in 'girl mode' lest I be completely outed at work.
My work has me in a semi-visible position (quoted in newspapers, publishing my own work), and I will need to undertake a major job search in a year's time.
I have to coordinate names and gender designations across two federal states and two countries, and my visa, passport, and work contract are tightly bound together.
I have a very deep voice. I have easily gotten it up to about 130 in pitch, up from 90. I have to work very hard to get it any higher.
Things which are ambiguous:
My family is ambivalent but I've heard of far worse. The bad side of this is that now they'd have our family name associated with trans issues.
I have a boyfriend who is not exactly supportive, but he's stuck with me this far.
I identify as transfeminine but outside of the gender binary. I know that the most 'feminine' I can hope for is a sort of a soft butch thing. That sounds pretty nice.
-C