Reinstated and then fade
Getting reinstated just so you don't have to explain to a date why your family doesn't have anything to do with you seems to be a very silly thing indeed. In my mind you'd have more to explain about why you have to pretend to be a JW when around your family. I'm sure you'll find that there are plenty of girls that will love that they won't have to worry about meeting your parents and dealing with in-laws down the road.
You'll probably also get more respect for having integrity in spite of the fact that it comes at the cost of your family. It's part of what makes you you and what makes you an interesting person. Everyone has a past, it's not your fault you were (presumably) born into a cult. It's not shameful that you were in a cult, it's remarkable that you escaped.
What's more is that exJWs don't have a monopoly on estranged families. It happens all the time. You're not that unrelatable, and chances are you'll find many who have a either experienced strained relationships, or know others who have, due to religion. Maybe not as extreme, but your situation is far from unique.
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.
Being a JW in the past is not something you should be ashamed of, as if you were a criminal or something. Once you are in a relationship where the issue of family comes up and you feel you can trust them, you can talk about it. Just be honest, as honesty is a crucial cornerstone to any successful relationship.
You can say something like "my parents/family are JWs and I decided it wasn't for me but their cult doesn't accept freedom of thought and choice, so they shun me. That's what their religion tells them to do, as crazy as that sounds. So we don't have a relationship because of that. Not my choice, as I would associate with them no problem but they are told they are not allowed to have anything to do with me, to pressure me, through emotional blackmail, to go back."
She'll probably be shocked and disgusted, as everyone I've ever told that to has been. But they'll be understanding and they'll not hold that against you.
The best way to give that cult the middle finger is to live a full, happy life on your own terms.
Thanks for all the comments much appreciated and more supportive than my crazy jdub wombat family
Just tell any girl your family are full on religious nutters that you were once and left it behind and leave it there. There are a lot of very dysfunctional families in the world so any half way intelligent girl will see yours as just another one.
Get reinstated if that's what you need to do , then fade. No need to loose family over this cult.
When you start a relationship and it develops the other party may not want to have much to do with your family anyway! Could be a bonus for them.
Its bigger in your mind than anywhere else. I personally think your idea of reinstatement to appear to have a family is ludicrous, but whatever works for you....a woman is going to love you for who YOU are...not your relatives....you.
Getting reinstated, then fading, will produce almost the exact same conditions you are already experiencing.
Do you want contact from a group of people that is based solely on the shared idea that you both believe in pet pandas in the "right around the corner" future?
You said "I am a man" Start acting like it and realize its time to put away childish beliefs and childish family members that cut you off simply because you don't think the same way on absolutely 100% everything. They are literally not worth a moment of your time. Cherish the good memories and move on.