So, I've got a bit of a debate that's been going on in my head for a while now, and I find myself a little stuck as to what to do. I work at a small manufacturing company in what I suppose you might call the "Deep South" (it's pretty hard to get more Southern than Florida) and I've been considering lately if I should come out to my coworkers. When I joined up with this company, I was in a semi-passing state, e.g. I dressed as a man, always had male haircuts, but gave my birth name out of habit and let people use female pronouns without too much fuss. Now that I'm really starting my transition, especially after starting HRT a couple weeks ago, I feel this urgency to present as male full-time, including at work.
I have told three people at work - my HR manager and my two direct supervisors - and they've all been pretty accepting of it. However, they've all been females and were all fairly young, mostly mid- to late-thirties. You might not think that terribly young, but remember: I live in
Florida. Most of my coworkers are in their 50's+. In addition, most of them are pretty conservative and heavily religious, and I'm sure you can see why this would cause me pause. There's one individual in particular - an older man, ex-military, thinks he's right about everything - that I'm worried about. He's already proven insensitive to transgender issues, as evidence by the way he occasionally berates Caitlyn Jenner any time she shows up in the news (still insists on calling her 'Bruce' despite being corrected by multiple coworkers, ect.) and this has me fairly worried.
To add just one more complication to this issue, I actually don't plan on staying at this job through the rest of the year. As soon as I have my legal name changed (which I'll be filing the petition for this week) I'll be applying for training as a CDL A truck driver. Glamorous position, I know.

But it'll pay the bills. The thing is, I want to hold off on actually going off to this training until after my next appointment with my endocrinologist, which is in June. I'm going to milk these UnitedHealthcare perks as much as I can while I've got 'em.

So, that leaves me with about three months on T at this current job, where I will have to endure the constant "Hi, Amanda!" every time I pass someone in the halls unless I speak up, and the possibility of our company Jarhead being your general jerk because I've started growing a mustache or something.
So, opinion time! Do you think I should speak up about my name and pronoun preference and try to educate the thick-skulled Sgt. Slaughter over here, or just keep my head low and endure being referred to as a female until the summer?