Something I've been noticing lately is that I feel almost... guilty for questioning my gender?

A close friend of mine is also a trans guy. He came out to me a few years ago, shortly after I had first started questioning my gender. He is only out to a handful of people because his parents are very transphobic and strict about adhering to gender roles to the point where he can't even buy a t-shirt from the men's section without them losing their ->-bleeped-<-. Basically, he's very much in the closet and won't be able to come out until he moves out and isn't financially dependent on his parents, which won't be for a while.

I, on the other hand, know that if my questioning does in fact lead me to realize I'm trans and if I were to come out, my parents would be supportive. My dad gets a little weird with the whole trans thing, but like not outright malicious just misinformed, and if his kid turned out to be trans he would try to understand and be accepting. I already frequently buy and wear clothes from the men's section. I'm in a position where I could cut my hair, ask people to call me by a different name, and present as male if I wanted to come out. And I kind of feel like it would be unfair to my friend, who isn't in a position to do that right now. Like, even questioning if I'm trans is somehow unfair to him?? My brain is kinda just going "how dare you question your gender when this person, a Real(TM) trans person, is struggling and stuck in the closet."

There are several truths you need to understand. Calling your friend a true trans doesn't say if you are transgender or not. I suspect you are transgender however you haven't reached the point were you fully understand your feelings.

Life isn't fair and some of use face a more difficult path than others. You can't trade your life for theirs but you can be there for your friend giving support and whatever help you can. Often it may not seem to be enough but there are limits to what you can do.

You need to take care of your needs first so you are strong enough to support your friend. Conditions change and it's possible the future will provide the opportunity for your friend to receive treatment. If not, with your help, your friend may be better able to work toward that goal.

You have nothing to feel guilty about and I suspect you are making a difference just by being in your friends life.

Different people have different situations to deal with. That's life.

I've felt the same way, being friends with several other trans guys. But the thing about it is that no matter whether your friend gets jealous or upset with you, it's a situation you can't help, just like he can't help the fact that his parents aren't supportive of him.

I say you should continue to figure yourself out, and be who you are when you come to a conclusion. Regardless of what he thinks, you're you, and you shouldn't suppress it over feelings about other people! I feel like that's what a lot of trans people deal with at first, the guilt of changing things because other people may react badly.

My point is, you're you, and you'll find out who that is in time. But you shouldn't feel guilty about being you, no matter who it upsets.

Seems a bit like survivor's guilt, I don't have a similar situation in my life, but really I wouldn't let that stop you from "surviving", I wish I could say I knew how they'd react to their child's friend coming out as trans, but that could become difficult too, so it's going to be a judgement call.
You say you're still not sure, but from here it sounds like you've made your decision, and there's just this one last issue, and it's a hard one.