Sure, you might have told her sooner (though just when? These aren't the kind of things someone spills on the first date.) But it would be reasonable for her to expect you to tell her before you slept together, or if things were moving fast, a week or two into the relationship. Maybe it felt too early to you even then? or maybe you wanted to have some time with her so she could get to know you before she heard the whole story? I will suggest that even if she felt manipulated by your waiting to tell her, it's what you told her, not when you told her, that is probably more of the problem.
A lovely woman who came from a neighborhood with gangs, completed college, and became a teacher (a respected profession with career solidity) has shown character and determination at least as impressive as her beauty. She'll have choices in who to date and who to marry. You might be the world's most charming guy, but the bombshells you mention are baggage other guys she meets might not have.
Your being divorced probably didn't count against you, unless you're still entangled with your ex. (Or, unless one of the convictions was for domestic battery.) But simply having being married before and not being married any more, is not a deal-breaker. After all, it shows you're not afraid of commitment.
A conviction at age 27 can't quite be shrugged off as boyish foolishness, the way a conviction as a teenager might. It's a shame this past is not more distant, 5 years ago is not 15 years ago. On the other hand, you say you have moved on from criminal behavior and are successful. So, probably that isn't what bothered her the most.
My guess would be that the "possible" child would be the straw that broke the camel's back. Do you mean someone is presently pregnant, and you don't know yet if the child is from you? If so, she might wonder why you haven't done a DNA test yet (they can be done when the woman is pregnant), how close you intend to stay to the woman who is pregnant, and what that woman's intentions are regarding you. Or is this a child who is already around and you simply suspect you're the biological father? That has its own pitfalls -- the question then becomes why didn't you do a DNA test long ago, and man up if the child is yours? She's going to be looking at you as possibly the father of her future children. She'll want to know you're solid and would never be casual or leave your kids to the fates.
Anyway, the divorce stuff and the jail stuff -- if you've cleaned up your act and have a good future, in ten or fifteen years nobody will care. But if the child is from you, (barring unforeseen circumstances) you'll always have a child that didn't come from your relationship with her. A lot of stuff comes with that ... not the least, dealing with that child's mother for eighteen to twenty years over custody, scheduling and managing visitation, and money for child support going out of your family's budget to support the child.
If she is annoyed that you didn't spill all of this earlier, it's because you didn't tell her until after you'd cuddled up. She might be feeling a little bit manipulated, even. It will be up to her to decide how important all of that is.
My suggestion about "how long to wait" is, she might be judging how serious you were about her -- dating someone else tomorrow would make you look like you totally were not serious. But pining or hoping for months would be stupid, she might already have moved on. So, it seems reasonable to give it a month or so. If you don't hear anything from her in that time, you probably aren't going to.
The relationship didnt sound very ideal to me. You told her the truth and she couldnt handle it. I wouldnt wait one more minute. If there is no trust the relationship is doomed to fail. That honeymoon stage can play real havoc on our brain. At some point you will see the reality of what this relationship was all about. There will come a time when someone will walk into your life and accept you and your past~Just keep being you~