I know how it feels to have transition far away (it took me like three years to get on T), and I guess my best advice would be to just take it one step at a time. Even though it feels very urgent when dysphoria is looming, it's not a race. If you plan on asking people to call you by your new name, I would highly, highly recommend legally changing it once you've settled on it. I am also very non-confrontational and asking people to use it was sometimes difficult. No one really gave me a lot of heartache over it, but it was still stressful for me. Having it legally changed made EVERYTHING so much easier, because I never had to worry about being called the wrong name, say, at the doctor's office. Or school - I could simply identify myself as my legal name, and since it was on the roster, professors and other students just never knew otherwise. Honestly, when you are ready to take that step it makes a phenomenal difference in how you go through the world and you feel a lot more comfortable because you don't have to worry about giving every new person you meet the explanation.
In terms of people you know, if you don't want to come out to everyone right away when you go by your chosen name, you don't actually have to tell them you're trans. My legal name is 100% male (a rather 'traditional' male name as well), but only a few people have actually said "isn't that a guy's name?" I assumed most people would "figure me out" upon hearing my male name, but most people just assumed I was a girl with a weird name. Lol. I even know a guy named James, who pre-T would get "...James can be a girl's name too!" Few people really think about trans men because they have the stereotype of the MTF who doesn't pass when they think of trans stuff.
