How about a new translesbian?

Hello everyone!
This is the first time I've been on a forum, I've observed a few while looking for answers and I think I can figure it out- the mechanics of forums that is. With regards to life as I know it, I have no idea what I am doing. Given that I have come here searching for general advice it seems prudent to give the full back story.
Once upon a time (12 months ago), I had a nice, small group of friends that were honestly more than I could have asked for. It was the kind of thing where you wouldn't get up to hand them a water bottle but you would give them a kidney if they asked- but never admit it because you didn't need to. I had 5 such friends and a network of a dozen or so associates that anyone else might have called friends. I have since fallen out with every one of them. At first there was no effect, I had always thought of myself as a loner but after about 6-7 months the total lack of conversation is beginning to take its toll. I can't talk to anyone anymore. With regards to my family, I will tally it up for you- my father makes fun of transfolk if the topic ever comes up and regularly knocks people for stepping too far out of the gender norm and any statement or reaction stronger than a sarcastic statement is deemed "dramatic" and therefor has no place in civilized society- My mother is a nervous wreck and would probably never be calm again if I came out or told her anything of great importance to me. My older brother is rather similar to my father and tends to follow along when dear old dad tells a something-phobic joke. I never really see my sister and my half-brother has not talked to the family for almost two years after saying "Surprise! I'm getting married!" after around 5 years out of contact.
If you are observant- or not brain dead- you may see that I am now left a little isolated- alright, maybe very isolated- and may be wondering "But Odd One, why don't you just poke around the college? I'm sure there is someone worthy of note..." I have tried the library, it is a reference library and as such has no one there for anything but studying and therefor will bite my head off if I disturb them.
This may be a good time to say that I have a rather irritating hatred of double standards on virtually all levels of life. This is what led me to avoid disturbing people in the library- I would destroy anyone who broke my train of thought in a place dedicated to a continuing train of thought.
Moving on, the people in my regular classes are generally either boring, insufferably annoying, too loud or some combination of these and other undesirable traits. The people in the classes relating to my certificate- and therefor the most likely to have regular contact with- will very rapidly go from "friends" and "helpful associates" to "competition" due to the limited number of jobs in the field.
On top of these rather bleak social conditions, I find myself in a rather uncomfortable position with regards to gender and orientation. By this i mean the issues that this site was made to deal with. I am stuck living in a family of low general tolerance, going into a field of low general tolerance and I am presently facing an increasing desire to- shall we say, change things up a little. By things I mean my gender by the way. Oh yeah and by the way it is such that a lot of transfolk do not even deem people in my particular circumstances to be trans, just straight men. And the coming out as lesbian adds one more thing on top of the already rather crushing pile of anxieties I get to deal with.
At present there is a plan regarding most of my major plans in life. The timeline should look something like this- Present or T+0 years: Working toward certificate, unemployed, presenting M.// +1.5 years: Begin working in field full time, still presenting M, begin saving for transition. // +2 years from now: Begin flight school on weekends.// +2.5 years: begin slowest possible HRT treatment.// +3.5 to 4 years: Move job to different facility in Washington, far from family, lose touch. Begin bush flying classes and possible start going F full time, depending on environment.// +5 to 6 years: Move to Bethel, Alaska with completely new name and that one little letter on official papers and, begin flying for a living with no one having any idea what I left behind.
To clarify, yes, I have every intention of leaving my family and the industry I am studying to get into behind to basically live out of the back of a very small plane in a hostile environment. It may be worth mentioning that the industry I am working toward will get you to a 6-figure income in as many years. It should also be noted that the company that I may work for soon does extensive research on their employees and, given the rather unique problem set of mine, you may excuse my not saying what field it is I am going into.
Unfortunately these challenges are not entirely pertinent to the main topics of this site but, given that they are all significantly magnified by the translesbian factor, this seemed to be the best place to start.

Quick recap- Translesbian 18 year old aspiring specific-field engineer with no friends and a family of limited usefulness with intentions of leaving the lower 48 states to live under a different name as an air taxi pilot in Alaska. Let me know if you've heard that one before.

For those that skip to the end, the problems- should you choose to address them are:
1) Trying to be alone without being so horribly lonely

2) Relationships- Should i search for an SO in college as I am or is it better to wait until I am further along the line to transitioning (Which will not even begin for another 2-4 years)?

3) Possible ways to ease family into the idea of me being trans, if it comes to that

4) Advice regarding acquisition of makeup and clothing items and how best to hide them whilst living with parents

Please excuse the rant but some things just needed to be said. Please advise.

 

Thanks for the welcome everyone, it really does mean a lot. I will repost to Gender Identity and Expression later on per your recommendation. Again, thank you all.