That list looks
real negative, and wouldn't deter me 20 years ago, 5 years ago, and expecially now. Here's my thoughts:
1. Educating people about transgender issues will be a part-time job for you, for the rest of your life.
I would help any way I can, but I won't go out of my way and say "look, here I am".
2. You will be discriminated against.
Been there done that.
3. Passing itself can be hard on your spirit.
Probably not.
4. You may have difficulty finding employment.
I don't care if I have to waitress or do odd jobs if I can't find employment, and I'm through with transitioning. Chances are I won't once I find out how to transfer education documents into maybe a new name.
5. If you found cross-dressing erotic before transition, that will probably go away when it's not cross-dressing any more, it's just normalcy.
Kinky clothes will never be out of fashion for me.

6. You won't ever have a normal body of a member of the opposite sex.
It'll be good enough in my mind.
7. There's no guarantee that your body dysphoria will ever go away entirely.
I think it might. It's a guarentee it
won't if I do
nothing.
8. If you do get surgery, it may be less than ideal. It will hurt. It will certainly cost a lot.
My mental and emotional pain are far greater than physical could ever be. When I got electrolysis, I couldn't believe it was actually painful to some people. I understand for surgery I will need to be cut, bruised, etc, but that will heal.
9. If you enjoyed being naked in front of people before (we're assuming that it was in appropriate places), that will change once your anatomy is gender-mixed.
I think I'll get by.
10. Your dating pool will shrink drastically.
Couldn't shrink even more than nothing.

11. You may lose your family.
If I lost the ones that held me back for so long, I have no problems with it.
12. You may lose many or even all of your friends.
One day, they might know, or maybe not.
13. You may lose your children.
Have none don't forsee a chance to have any anyways.
14. You may lose your religious community.
Zero problems here.
15. People will ask you rude questions about your genitalia.....for the rest of your life.
I'm not going to wear a shirt that says "sex changed".
16. Statistically, you will be much more likely to be assaulted and/or killed by hatemongers.
I am more than capable of protecting myself at any time.
17. If you do go to jail, you have a higher likelihood of being killed while in prison.
Too smart for that.
18. You will have trouble finding medical care.
I am still wondering about this one.
19. Being on hormones usually means being dependent on a substance created by large, corrupt pharmaceutical companies for the rest of your life, especially if you've had your reproductive organs removed.
No more dependant than anything else, like food.
20. There are certain parts of the globe that you can absolutely never visit because of the very real possibility of being jailed or worse at customs.
If it's that bad, there's no benifit of being there in the first place, unless there's some kind of apacalypse. In that case I'd find away around it.