There are no clear cut answers in life.
We are all, in some way, lost and trying to find our way home. But, the more lost we are, the more we learn about who we are and where to go from here. To Quote Henry David Thoreau:
Lost, this is my reality, my philosophy and my namesake. As such, I do not know what guidance I can give you, but I will try my best and answer those questions in which I hope I can give you some direction. For whatever the advice of a cis-conforming asexual crossdreamer is worth.
"How can you know if you are trans?"
Simply put, we can't ever know. But, what we can do is be honest with our feelings and make the best guess possible from there. It took me 2 decades to reach the point where I could be honest with my own feelings. I deeply deeply wish I was a girl. Does this make me trans? I don't know, but from everything I have learned about the issue, and about myself I would have to say "yes, it does." That is my own personal truth. The direction I have chosen to find my way. No it doesn't. What matters is being true to yourself, true to your own person truth. In the end, "trans" is just a label; and labels are just tools. How much and what use they can be is up to the individual. For me, my labels are a way to communicate my truth about who I am to the world. Whether the world accepts it is not up to me. If your only reason to transition is because you, or someone else, put a label on you; then my answer is a resounding "no, you shouldn't." Making a decision based upon what other people think is right, or making a decision just because they have put you in a box is destined to lead to heartache and ruin. It is a giant sign post pointing to despair.
"If I am should I transition?"
Rather, whether or not you should transition should be a decision based solely upon what YOU want to do. I believe you should only transition if that is what you truly desire to do. It is something that you need to be willing to sacrifice for. It is something that you need to be willing to accept all the consequences that come along with it. This is no easy question, and in the end it is something only you can decide. But, however you decide, know that you are not alone, and know that you are not broken. Though you may not see us, you will have sisters and brothers in dream who support you.
Regret is a part of life. No matter which path out of the fog of life you choose you will have regrets. Therefore, asking if you will have regrets is the wrong question. The question you need to ask yourself is what will you regret more? Taking a risk and failing; or, not having tried at all. There is a Latin saying:
"Will I regret it? What if I do?"
Not even Jupiter (most powerful of all the Gods) can recapture an opportunity once it has passed. This is your opportunity; will you let it pass you by? For once it has passed you by, it may never come again. Live as you are now or live as you truly want to be. Your decision..
And when regret does come, you have two choices, to let it weigh you down so that you sink in the Swamp of Sadness, or accept it and let it pass through you so that you can move on.
"Will I lose everything? Does that matter?"
For everything that is lost, something else is gained. Again, this is the wrong question. Both directions lead to loss. The question is what do you have now and what will you gain; and which is of more value? The answers to these questions depend upon you and your own personal truths. Do you have something in your life that is so valuable to you that it is worth continuing to live as you are now? Or is losing the chance of being who you want to be worth what you have now?
For me, I have things I value too much to take that risk currently. But, who knows what the future holds.
"What am I so afraid of? "
I think you fear what we all do; that your decision may lead you away from happiness that you seek. Not only that, but in such a way that you won't ever be able to return. You fear the unknown consequences. And, to be sure, I believe there are very real consequences to one's decision on this. Rejection, isolation, persecution are all real things we could face. It is not only natural, but wise to be afraid of these things. Fear is not a vice, but a virtue.
But courage is an even bigger virtue. And by courage I don't mean idiotic male bravado. I mean true courage, standing up or doing something because it is the right thing to do despite being scared to death of the consequences.
This is something I worry about constantly. Yesterday, for example my mind was ablaze with transgender fantasies and the desire to be a girl. A couple of times I had to fight off tears. Then later that day, the feelings vanished and yet once again I was left wondering "what the F*** was I thinking." It definitely feels like I am losing my mind at times. But, if that is what is happening, there is nothing I can do about it. I just have to accept these thoughts and feelings as they come to me. If my personal truths about how I feel conflicts with that same personal truth two minutes from now, then so be it. Because, no matter what else it was, it was true at that time.
Is being trans why I get so depressed, and have panic attacks. Is it why I am so self destructive?
I don't know. As far as I know that could be part of the case. But one theme I have noted in all the transition stories I have heard, is that many transwomen expect transitioning to fix all their mental and emotional issues and it almost never does. Personally, I think what you describe is too complex to have just one root cause. Yes, being trans could have contributed, but many of those thing you mention tend to have other causes as well. Some of which are just inherent traits with which one has to deal with all their life.
Am I just gay? If I am why aren't I attracted to gay guys? Is it because I was abused... because my mother hated me?
Anything is possible, but I can't possibly answer these questions for you. What I can say with a degree of certainty, is that feelings like these are ambiguous and hard to understand even for those of us who were not abused. I spent years trying to fit myself into a cis-heterosexual mold and no matter what I tried, my piece of the puzzle just never fit. I would suggest that if it doesn't feel right; then just admit that and move on. Just because you don't have the name for it today doesn't mean you won't discover the right term tomorrow.
Maybe I am an addict because my parents and siblings are addicts, and not because I am trans? How can I know? Why don't I know!!?
I believe addiction is a disease. But, I also believe that being trans is not. That said, I don't think there is any way to know anything 100% for certain. Again this is just the way the world works. Our minds, our bodies, are limited in what they can do, in what they can know. We are stuck trying to figure out if we got all our pieces in the right place to a picture puzzle to which we will never have all the pieces.
I feel we are ultimately just beings who exist in a world without rhyme or reason and that the only meaning our very existence has is that to which we make ourselves. This is our existential reality.
Is not knowing a sign I really am not? Why did I say I wish I was a girl instead of I am a girl? Is it important? If I really am in the wrong body why didn't I feel that way every single day?
I don't think it is a sign of you not being trans. I personally believe that some people have a stronger sense of internal gender and that most of the rest of us do not. It is like being able to see or hear. Some of us have more acute senses than others. I also believe that those transpeople who say they "are a girl" or "were born in the wrong body" have a stronger sense of internal gender than you or I do. Thus, while they can be certain of their feelings we are left out in the woods trying to simply make north from south of our feelings based upon the most nebulous of signs like our crossdreaming and unhappiness.
For cis-people this acuity of internal gender is not important. It might cause feelings of "manliness" or for a lady to say "man I feel like a woman." But for most, I bet they are only cis-by-default. They just believe they are a certain gender because that is what the mirror and society tells them. It is not based upon any real feelings.
Was it because I was too drunk to realize? Why does it come in seemingly random waves combined with depression? Am I just lying to myself? WTF is wrong with me?
I don't think there is anything wrong with either of us. Could your alcoholism have caused you to miss the signs? Maybe, but then how do you explain people like me who feel the exact same way but have never been drunk.
Once more I don't know the answers but I suspect the waves we feel are the result of coping mechanisms we employ. When we were younger they were stronger and more robust. Now, however, they can't keep up with the progression of our dysphoria and are starting to break down. I believe this causes the wave feelings we all experience.
And I think the depression isn't because of us being trans, it because our bodies and the expectations of the world are at odds with our minds.
Do I just want attention? Do I just want to be treated how I imagine a woman gets treated with no real regard for the realities of actually being one? Is this all in my imagination? Is this all a creation of media manipulation via wanting to be a princess, A special snowflake.
I hear these type of thoughts and accusations all the time as an asexual. People trying to tell me I am not real and just wanting to be a special snowflake.
My opinion is that these thoughts are just society's ways of trying to make you invalidate yourself. You hear these types of allegations all the times from bigots and the over privileged in an effort to gaslight you and convince yourself to contribute to your own erasure. Your feelings are real; you should know that better than anyone. If one wanted attention or to be a special snowflake, there are better ways of doing it that doesn't cause all this anguish and self-doubt.
For instance, I write in cyan/teal. This allows me to distinguish myself and show my own special personality in a way of my own choosing that empowers me. There are myriad ways of doing this that doesn't put one at risk of losing family and friend, that makes one a target of derision and rejection. Why would anyone choose to do that to themselves?
Be true to yourself, to your feelings, to what you believe and then these type of thoughts will vanish.
Is being a woman about thinks so superficial as being pretty? Conforming to some caricatured gender norm? If I was really a woman wouldn't I cherish the power I currently possess to effect positive change in the world for others, and accept the realities of the now. Would I focus on concepts of empathy and compassion and love and kindness? Is that even what being a woman is cause I sure know a lot that are none of those things.
Is that what it means to you? Cause the type of woman you would be is completely up to you. As it is with everyone woman. Everything else you list is malleable and changing.
In fact most of what you listed wouldn't even apply to me. Cause, the part of me that wants to be a woman is not something I can change. No matter how hard I try, I cannot even imagine myself as anything but a woman erotically. To even begin to feel those emotions I have to turn control of myself over to the girl inside.
And even when I am not trying to turn control over to her, she takes control of me sometimes. Regardless of if I want her to or not. The fantasies and the dreams. The longing and the despair. I can't control them. It is not about "what does being a woman mean?" It is about the fact that my brain sees it self as female. At least it does in part. And that part is a very vital and important part of me; and most importantly a part I can't change no matter what.
Is it worth the money? Am I too old for it to work? Will I lose my job, and be homeless? Will I ever find true love?
Whether it is worth the money only you can decide. How much is it worth to you.
What does age have to do with anything? Some people transition in their teens and find happiness. Some in their twilight years.
I won't lie and say your job is safe. I don't know where you live, but in many parts of the US there are no protections for being trans. To figure that out you need to know the people who you work for or work under.
Finding true love? Is there even such a thing? If there is true love, what does that make all other love? What is the difference? Is love ephemeral? Or is it eternal?
Sorry, but you are asking someone who questions what romantic feelings and love even are, who struggles to differentiate friendship from romantic feelings, and someone who doesn't even know if they have the capacity for that kind of feeling. I am probably the last person to ask this kind of question.
But I do know this: There are trans people who claim have found this romantic love thing and live with their beloved until they die.. There are cis-people who never find a person like that no matter how hard they search. There is no knowing unless you try and find it on your own.