Patrick,
Thank you for a thoughtful and challenging post.
It has been said on this Forum that Freemasonry is an institution devoted to making good men better, not for reforming bad men and making them good. This is a somewhat harsh truth, but the fact remains that our membership is not comprised exclusively of saints and angels. Most Masons, I believe, would tend to have consideration for a man who grew up in a poor environment, lacking proper guidance, and may have been led into an unfortunate and even criminal lifestyle. You admit to a criminal record at an early age, compounded by other incidents extending over a period of some years. You now appear to be making the best effort you can to be a law-abiding and productive member of society.
If you were to approach me about membership in my lodge, I would want to feel that you have finally and definitely put all that behind you, that you are committed to leading an upright life and and providing a wholesome lifestyle for your family. Your open and honest revelation of your past is an essential part of what you would have to do.
I do not know what the regulations are in KY regarding a stained past record. But if you have made yourself into an upright man and are looking for a way to join and associate yourself with respectable men in your community, I encourage you to try to join us. It would help if you know a Mason who will be willing to sponsor you. Lacking a sponsor, you could approach your local lodge and introduce yourself as someone who would like to join. In any case, the worst that can happen is that they won’t accept you. {If it were me making a decision, I would certainly be inclined to give a break to a widow’s son and an operative mason.)
So give it a try. I wish you the best, and hope you will let us know how it turns out.