Hi Morgan-Kate,
You said you are double insured - who is your plan through? I'd encourage you to take a look at the plans under the Affordable Care Act and see if there is something offered in your state that will work for you. I've had plans in both Virginia and Washington DC and they've both covered my HRT, doctor visits, mental health, and surgery. Look at the terms of each plan and make sure there are no gender transition exclusions. Many doctors, especially ones that work with trans patients, know how to code visits to make sure they are covered by insurance.
As far as living arrangements, take a look at the Trans Housing Network on Tumblr. People can post if they're looking or if they have space available. You could submit a post and let people know that you and your friend are looking to get a place together. It's always cheaper with extra people.
I don't know of any organizations off the top of my head. We do have a good informed consent clinic in Richmond, VA. I believe they do things on a sliding scale, so you'd only pay what you could afford. I'm not sure what all that applies to, but it would be something to look into. If they are anything like the clinic I go to in DC, they may have additional free services. I got to meet with lawyers for free to process all of my document changes. You could look up the closest PFLAG chapter or LGBTQ support group and see if they could refer you to any other organizations that offer support.