This is an interesting topic, with some very interesting posts.
@Keri, I do agree and sympathise with a lot of what you say. In fact a lot of it is a breath of fresh air, when so many posters can be uber enthusiastic about everything now being awesome post-transitioning. I know that's not the case, so when I read someone else saying so, I immediately connect.
I too pass, and I am very lucky indeed for that, and it is luck + effort that does it. But it doesn't always mean I'm happy and grateful to be alive.
Yeah, getting hit on got old with me too. When I was younger I got a lot of attention from men, and I also played up to it, loved it and dressed provocatively. I enjoyed it at the time, until I got into hot water. I was learning how to "handle guys" as a crash course in a short amount of time, no-one realised when I had just transitioned that I hadn't got a lifetime of past experience to help me. I naively thought I could have lots of male friends (like I had before), but I didn't notice initially that they saw me as something else. It was only when guys actually fought over me that I finally realised what was going on, and how wrongly I was handling things. I really miss that part of my old life, having good close male friends with no other strings attached.
Losing male privilege is a little tough, but I found I was able to find the privileges I now had from being a female, and use them to fill that void. Being treated differently was strange at first, and then it was a massive ego boost as it meant I was passing, and then finally experiencing the cr@p that cis-women experience in life. Well that followed of course, and I guess I just have to suck it up!
Being a woman is extra hassle and work, I agree. But being a transgendered woman is extra work on top of that, at least for me. There are extra things I have to do and be aware of, that most cis-females don't have to. Sometimes the extra effort required really gets me down, and makes me feel that life is unfair and that I've been hard done by. Dealing with that can be very difficult, luckily my fella is very supportive and understanding of the issues and certain situations that are stressful for me. I miss the "just get up and go" hassle-free existence that guys generally have, but then, when I'm finally ready to face the world, it feels 100% better and just "right".
I guess I'm more moody and emotional. Although I wasn't a very tough guy, and I used to cry easily and openly before I transitioned. That was a real social no-no as a guy and I was frowned upon by my peers, but inside I wasn't so bothered as I knew I wasn't really a guy. I just couldn't hide it in the end. I've always been a bit "weepy", and after transitioning, I just got even more weepy, if that was possible. It can be a pain sure, but it's part of my character and always was.
I learnt the hard way about how vulnerable I now was as a woman. Another crash course served up by life! Yeah, I experienced physical, mental and sexual assault at the hands of guys. Goodness me do I now know how cis-women feel who have been through that

That initial naive innocent joy of finally facing the world as a female, I experienced that, but it was beaten out of me, and replaced with a feeling of being "damaged goods". <shudders>
But after all that, I cannot change my biology, I like guys and I cannot lie <blush>. Luckily I now have a wonderful supporting man in my life, and he's helping me to rebuild a lot of my lost confidence.
One thing I don't agree with you about is driving. I was a trained test-driver with extra driving licences and permits I used for my old job. After transitioning, my driving improved because I am now calmer, and don't speed. I let road rage of others just pass me by. And since transitioned and had my op, I have gone on to add a lot of other driving licences and skills to my remit. I got my pilot's licence, I got a truck (HGV Class 1, artic) licence where the truck driving examiner told me I was the best driver he had ever tested in his 18 yr career. I got a fork-truck licence, I regularly skipper a steam boat, and I drive steam trains too. I think my driving has got better since I transitioned.
Really it's the
"OMG Should I have done this, Yep, I go there.. it happens.. I cry.. sometimes hard.. Its like why did I have to be a woman,.... ->-bleeped-<- its hard and I lost so much" bit you wrote which really struck home with me the most. I totally have moments like this, and yeah, I get depressed about it. But really when I think about it I had no choice, and I don't regret it, but yeah it's difficult and I miss some things, but I've gained more than I lost in retrospect.
Thanks for a thought-provoking post.