I tried to do this, was working part time (~20hrs a week), nursing classes, transitioning too, and, I just couldn't do it. Halfway thru that semester I was totally burned out, always had something going on, somewhere to be, always tired, just done basically. After talking with a few advisers at school, people who know about my situation, was advised to drop for the semester, get things taken care of, get my stuff together and back on track again. Being that I had basically given up, I did that. I planned on going back next fall, start over again with a bit of a head start and with much less going on for me.
I really like the idea of starting with online classes at first if going to a campus class could make you uncomfortable. College is hard enough as it is, anything you can do to make it a bit easier and more convenient for you I'd say do.
If you decide not to go to college, I do think you should look for a job, even if it is just a part time, crummy job, make a little bit of money, because transitioning is expensive.. Go in whatever mode you want to go in, whichever mode makes you happier and most comfortable with.