There are some people, parents included, that simply will not accept you as your true self, no matter what you may want. You sound young. If that is true, then you may have to follow her rules to some extent, but the most important thing is that you stay safe! As long as she's not hurting your physically, then mostly everything else can be dealt with. It sounds like your friends are going to be your support, use them as such on those bad days. That's what friends do, help each other through good times and bad. If you can, ignore most of what she says. Transitioning is scary for many cis people, and she might not know how else to deal with it. I'd pity her more than anything. You "not being who she expected you to become" is probably scaring her, and her hurtful words is how she deals with "the unknown." Hopefully she'll come around someday to realize how much happier you are as your true self.
Is there a LGBT+ center near you that you can get to? That would be your best place for support and information. If so, go to it and as your questions about the medical side of transitioning. They may also have a transgender support group you can go to, if so, you should probably attend, if nothing more than to vent out your frustrations, not to mention they may be able to give you info on who/where to go to (or where/what doctors to avoid.)
In the meantime, you can wear what you want. Hit the thrift stores and go to the men's section, I bet there are plenty of clothes there that may fit you. Start dressing in what feels "right" to you, and maybe invest in a binder. Be sure to follow the advice on how to wear one safely, you can do serious physical damage to yourself if you don't bind properly! There are plenty of threads all over here and in the FTM section on how to wear one safely.
Don't worry about "having feminine eyes" or "curves," HRT could change that. And don't worry, not every man has "the man brow ridge," or whatever. There are a LOT of cis men that look somewhat feminine, are short or have tiny bodies. Carry yourself with pride, and people won't notice how tiny/feminine/short/etc you are! If GRS is something you're interested in, you can research here and all over the web on what kinds are currently available, and what can happen when you take HRT. Your facial structure, fat distribution and musculature will definitely change, no matter your age. Facial hair, and other things will depend on your genes, but are more than likely possible as well.
To answer your questions, no, unfortunately, parents/siblings/etc are not required to respect your pronouns. But, you also don't have to take them misnaming/misgendering you. I correct my family members (and anyone else) when I'm misnamed/misgnedered.
If you have your own insurance, no they do not have to be informed of when you start insurance. If you need your parents' permission due to being underage or still of their insurance due to college, for example, they may need to be informed. You can always check by calling the insurance company to see what their policies are. Have a list of your questions ready and take notes of their answers so that you won't forget them.
You can come out to your family whenever you want. Whenever you feel most comfortable doing so. Some people come out before they start transitioning, some come out during, and some after. Its all up to you. Sometimes, a letter is the way to go, that way you can say whatever you need to say without fear of interruption. Keep a backup of it, in case they tear it up/delete it. Sometimes, sitting down and talking is the way to go. A simple discussion sometimes works. Or you can simply have them see and hear the changes, and they can figure it out for themselves. Again, its whatever route you decide to do.
As much as it may make your Mom feel embarrassed, she needs to realize that its YOUR LIFE. You will be the one living as male, female, both or neither. YOU. No one "allows" their kid to be transgender, you simply are. Its how you were born. She may try to force you to hide, but it'll eventually come out...if you choose it to. If you're worried about "having to hide your manliness, you can opt to wear t-shirts and jeans, for example. But once you're on HRT, chances are, your changes will eventually be obvious for all to see and hear. You doing "her a favor?" She should consider "your level of comfort," but unfortunately, sometimes parents can't/won't/refuse to see the forest for the trees. I'm sure that once your voice drops and you start growing facial hair, she'll no longer want you to wear dresses! You shoulnd't conform to "make them happy," they should be happy that you found what makes you happy. Of course, that's not what it sounds like is going on, thus the need for support groups and good friends.
Also, don't forget, there are plenty of people here on the forum to talk to/vent at/ask questions to, we're here to support one another as well!
It sucks that you are being made to feel ashamed for being yourself. If you can, ignore the looks, the comments and the anger. Again, its your life to live! The only person you have to worry about during this should be you. Everyone else will have their own thoughts, like them or not. During the bad days, that's when your friends and the LGBT+ center should be there to support you. You're not being "entitled" or whatever, you're simply dong what makes you happy and what feels right to you. That's not entitlement, its called living.
Whatever makes you happy is what you should be doing.
Good luck bro.
Ryuichi
