Late 30s here. I've been in and around trans* communities in some form or fashion off and on for about 15-20 years.
I think it would be inappropriate for me to comment on the site as to its outreach. I really don't even know how to begin thinking about an answer to the question because I'm not sure how to apply the concept of outreach to this site.
As to trans* people as a whole, I think we are like any group of people. Some of us are great at outreach. Some stink at it.
In the ordinary-person-not-doing-any-sort-of-work-on-the-issue part of the community, I don't think any outreach happens. Those individuals tend to--for very good reason--live by hiding in plain sight. Those who do not pass also seem to be very hidden and secretive. There are some interesting stats on the degree to which many trans* people stay holed up in their homes and just don't go anywhere for fear of harassment.
One might suspect that such persons are doing no outreach at all. And there's a lot of truth to that. But it's not quite zero. Those individuals can still do things like provide an insightful comment about an article on the Internet or be a "knowledgeable ally" in the workplace. You'd be amazed at how often I comment on
advocate.com, for example. And I always seem to get two or three responses from trans* people thanKing me for being such a great ally. Likewise, when I educate people face to face, I do so from a position of great knowledge, but using the pronoun "they" instead of "we." (In fairness, I sometimes use "they" for other collectives to which I belong too). So far I have not had a problem with that approach outing me. Some other people who aren't out do that too. Some are too scared. Those who do those little things are contributing to outreach in small ways. And small ways matter.
Then there is our activist community. I reject the idea that everyone has any duty to be out or to be educating the public. Doing that is my job and the job of others who have taken on that activist role. Not the job of John or Jane Doe trans* person on the street.
Where I live, the two major "names" in trans* activism are myself and Dana Beyer, whom you may know of. I'm known to some as the anti-Dana because of how polar opposite we are. When we do outreach and deal with the public, we are very radically different in how we do it. But is one of us "better" at outreach? I doubt it. Dana will educate you about one thing and I'll educate you about something totally different. But whichever one of us you meet, you're going to come away understanding more, being less ignorant, and being less hostile to trans* people.
I think the portion of our population that spends time going out and educating is actually pretty good at it by and large. Like Dana and me, their approaches may be totally opposite from one another, but there are a lot of them that really work. But the number of people doing this is far too small to meet the need for education. That's not a sign of being bad at outreach. It's a sign of how much work needs doing and how few are willing to do it. But that's normal in a movement, especially one as young as the trans* movement.
So if there are any aspiring activists among our group, they should know that I do take apprentices and if you come hang and work with me, you will end up in interesting places. So get in touch if you're local and I will put you to work.