So I started looking for work at the beginning of this week without much luck so far. I've applied a few places and hoping to hear back but we'll see. I used to work as a carpenter which was alright when I worked alone for a small company. I then worked for a union my last few months and I swear it was working in an environment like that which was really a huge factor in just making my dsyphoria explode when I had already had been dealing with it creeping back for awhile. I really never got in to that line of work by choice and really only did it at the time to support my family. Well that was really all besides the point lol but I just know I can't continue to do that as I began transition. I've been on unemployment since August but that runs out in a month so I'm really in crunch time. If it was just for me I wouldn't care but I've been giving everything I get right now to my ex wife even though we aren't officially divorced yet so I'm not sure how much I should be giving her but that's another story. I still feel so terrible about it all and need to find a job. I've been looking into everything from retail, food industry and I even signed up on this site for jobs that allow you to telecommute. I guess I just wanted to know where you all work that is maybe trans friendly perhaps. I've been trying to apply to places I know have trans coverage in their insurance polices for now as much as I can but like I said I'll take anything. Also I have not yet began to present full time and I was wondering if I should let my future employer know that I'm transgender or is that my own business? I'd love to hear what others are doing currently or have dealt with in the past. Sorry if that turned into a bit a ramble as always. :P
You could start with that list that HRC puts together about best LGBT workplaces. While they may not explicitly mention anything about trans people on their websites, by and large they'll have policies in place already which would work to your advantage. I applied to two places from those lists and while their gender selection was only male/female, they did let me put in a preferred name. The recruiters did not use it when they contacted me though. Seems to be pretty hit or miss.
As to the rest of your question, I work in hospitality consulting in Washington DC. No one at my company has ever wanted health insurance before, so part of my job currently is making that happen. As of right now I'm only partially out at work, but I don't anticipate any issues.
I also do some online work (maybe 10 hours per week) that has thus far covered all of my transition expenses (doctor's visits, testosterone, therapy, etc.).
Ultimately it's going to depend where you live and what the job market is like there. Big cities tend to have more opportunities, but you have to have the right skill set for a lot of things.