I think after some thought although I don't understand cis women, it would be easier to wake up as one. In my experience the boyfriends and partners I've had in life all just wanted to look after me, and people are just generally nicer to women and concerned about their wellbeing more. As hard as it is to live as a woman when you are not wired like one in the brain, I can see how it can make for an easier life with a better support network, with less expectation and responsibility placed upon it, with people accepting gender-bending clothing more on a woman and allowing her to express more freely.
So yeah, if I had the choice I suppose I'd rather be cis woman because my life would definitely be simpler and go pretty smoothly. I wouldn't have the clash problems with relationships and people would accept my profession and desires just fine.
But since I don't have that choice, this is just my idle speculation. Life's been pretty hard and miserable, so I'm biased toward wanting an easier life I suppose.