(Sorry, I missed this when you posted originally, hope my response is still useful)...
Yep, the psychologist I saw this time around seemed quite clueless about trans issues. I was originally referred to him for depression, I wasn't specifically contemplating transition... that resurfaced by the time of the first appointment though. A lot of his advice pre-transition - "have you tried wearing women's undergarments under your clothes when you go out" - seemed to come straight out of Treating Trans 101. He even talked about the need to present as female for a year before HRT (this isn't the UK or Europe, thanks) and when I asked if he had much experience with trans clients he said he had helped one person post transition, that I was his first pre transition trans person. He even referred me to another shrink for a second opinion, fortunately that one was greatly experienced in dealing with trans people and agreed to HRT after just one visit. I suppose if I'd gone to him first then I would have been on HRT much sooner but really the difference would have only been about two months anyway.
Mid way through the process I did find a counsellor at a Gender Center who was great to talk to about trans stuff, he was very supportive (obviously couldn't refer me for HRT though). I still see him every few months even though things are relatively good.
I still also go to the first psych that I started seeing - I guess though I don't really talk a lot about my issues with my transition, just personal problems (like family, work, etc).
On the balance I found that having some who was across trans issues was very useful. I was still able to make it work with someone who was more of a newb because at least he was willing to be open minded and supportive... sure, he occasionally said some naive almost offensive things but I was able to set him right. Ultimately he was there to make sure I was able to sort out my $#&%, not to sort it out for me.
I find though, with that kind of practitioner, as soon as you start raising doubts and concerns about transition they will almost always try to back you out of the process. Their logic being "if this is upsetting you then don't do it". What they don't understand, of course, is that not "doing it" is usually much, much worse. The gender counsellor, on the other hand, was able to make me examine my motives and my thinking (really helped me to root out and stare down my internalised transphobia and fear of not passing, for example).
It is always possible to steer therapy to your own benefit and having a clear realistic goal around it is going to pay dividends. You are an intelligent woman and I think you already have a lot of understanding about the issues involved with transition. For you it seems it is more about how the process is/isn't working for you, feeling that people are humouring you, that you don't "look right", that you are isolated in your journey. Make the therapy work for you around that - the practitioner doesn't have to have gender experience because many people (trans, cis, gay, straight, young, old) have those issues. I might suggest you approach any counsellor at college not specifically about gender but from the point of view of getting assistance around how you feel other people see you, about self worth, about feeling persecuted, about how to connect with people and how to move through difficulties. I might be completely wrong and I say this only because I care and would love to see you happy, but it seems those are the deeper issues at work for you and that your transition would benefit from that approach.
