I don;t think that that's the right approach to find out who has the harder time. I am born in, but in any way can I compare my process of leaving to those of other better families with better support.
People's lives are different. People's positions in the congregation are different (i.e., even though we were raise the exact same way as JWs, the story of my heterosexual brother is quite different from mine and from my sister as a female; the three of those types of people are treated quite differently in the congregation).
Also, people who have experienced life outside join the JWs for different reasons. You cannot compare a person who join to escape from abusing drugs and alcohol with a person who joins simply because they want to believe in something.
Same thing for the process of leaving. I for once embraced my leaving and saw walking away from the Jehovah crap as the best thing that ever happened to me. Others leave full of fear of the uncertainty, sad and depressed from disappointing loved ones. Some who have something to go back to may have good things and people to return after leaving the JWs, others don't because the join looking for a better structure in their lives.
It really is different from person to person.