Find it hard to date girls out here only due to always having this secret I carry with me that I was once a JW and the thought of telling a girl one day why my family don't acknowledge me as even alive.
What? I'd look at who and what kind of people you choose to date. Maybe stepping out of the comfort zone of people who make you comfortable asking out could help you find saner people who can't care less about being a JW. It's a religious affiliation, not child pornography for heaven's sake.
Some jerk elders love to mess with people and exercise all the power they can over others. That's all they have in their lives, so they may make it more difficult to you just for their own feeling of power over you. Have you considered looking for another congregation that may have more loving elders? I've known of some people who got reinstated faster in a different congregation, even when the written records trash them.
As for your reasons to get reinstated, I think that's decided on a case by case basis. I'm very clear about my standing with the WT and my JW family, and I don't need to go back for anything. But I know that there are people who are too invested and have many loved ones who are in and can't just leave and walk away. Your reasons are yours and I don't think that there's any right nor wrong in going back.