I'm going to take a leap here and assume your profile name matches your true gender, rather than your biological gender... if I'm wrong, please accept my apologies and switch gender pronouns and descriptions as appropriate in the post below.
It sounds like you might be in need of a sliding scale (or free) gender therapist. I've gotten some good help from GLBT support groups (free) in the past, if nothing else they have provided local, sympathetic ears and hugs when things got very grim.
I don't know your status in transition, whether you are comfortable going out as your true gender or not, but that has been a help to me as I await HRT. Going out, presenting female, and being gendered correctly by strangers is very validating, but being mis-gendered (the dreaded "sir") can be tough, so I recommend going out with a group.
It could also be helpful to cultivate CIS-female friends who are understanding... they can give a lot of tips on clothing and makeup, maybe even give you a makeover, watch movies, etc. There's something about being in the company of women *as* a woman that can really help me feel better about myself, and it's a great way to further your transition by picking up mannerisms, speech patterns, etc.
I'm wishing the best for you, and hope that your financial worries straighten out!
