I am a woman of trans experience, just went through my GRS surgery about 10 weeks ago. Being a transwoman doesn't necessarily mean you either male or female, but some are non binary or non confirming.
Look at it like the difference between a light switch (on/off) and a light dimmer. (On, off and anywhere in between)
Talking about my personal experience, I was and am, a woman regardless of what's in between my legs. However after receiving my surgery I feel much more happier and complete. Next to having a vulva now I'm equally happy to no longer have to see my old penis.
Having said that, there are quite a lot of (legal, mental and medical) requirements that one has to follow before being allowed to have surgery, which you can not get from one day to the next. Once you have reached the requirements than there is the cost involved. Yes some health insurance does cover surgery, but good luck trying to find a Dr. that accept the insurance. Most still have to pay upfront, and than get reimbursed from insurance, which isn't always the same amount as what you paid.
I am 3 years into my transition and the only reason I was able to have my surgery is because of some unknown lucky reason I received a loan offer, which I took. (The next 7 years I be paying for this)
I know, and have, female friends that are perfectly fine and happy with their penis, and I know some that are unhappy. I also understand that quite a lot of transwoman who work in the sexual entertainment industry, are not happy with their penis but need to retain it inorder to have an income. It also means they will not be able to constantly be on the correct hormone dose, as hormones, especially testosterone blockers, will affect the penis and testicles.
PS, there are also health risks involved, there is a 1% change to get a fistula, which can kill you. 20% change of problems peeing, and some will not experience orgasm. Although the medical technology is advanced, changes of something going wrong become less, it's still an important decision maker in wether to have or not have surgery. In my personal case... I had to have surgery.
Hope it's not to long of a reply. Hugs.