Family will be the hardest on you
Life was so much simpler when we were kids. We used to run around saying silly things like "You can pick your friends, you can pick your nose, but you can't pick your friends nose." Later on, this changed to "You can pick your friends, but you're stuck with family."
Whether you're lesbian, gay, transsexual, or some combination of all that, coming out to your family entails more risk than your friends, neighbors, or your co-workers. Your friends hopefully like you for who you are inside; if they decide that they don't like the "new you", it might be small consolation, but at least now you know you didn't lose much after all.
Your neighbors can either be supportive or not - that's up to them, but it's not like you have to deal with them all that much if you don't want to.
(original tree photo Stefan Wernli. surce:wikimedia.org)
As for your co-workers, worst-case scenario, you didn't really like that job all that much anyways, right? Sure, these are all rationalizations, but they work because there's a grain of truth in all of them. Real friends will try to understand; Nobody wants to work with co-workers who are jerks; and your neighbors can just mind their own business if they're not happy about it.
The thing I have found most challenging in my 10 years as a partner is the lack of support for family and friends of those who are transitioning. After Debbie and I met in 2000 I went online and spent hours reading peoples stories of transition and found it was common place for partners to walk away not understanding Gender Dysphoria.
