bjjkid, here’s my take on it: when my oldest started shidduchim we realized we had to figure out what our approach would be to a shidduch with a divorced family. We decided that if it was difficult matzav – triangulation, abuse, e.g., far beyond the tough time while breaking up and adjusting – the younger the child was, the more likely we would be not to consider it. There is so much stress on a young couple we wouldn’t add to it. However, if the parents were mentschen, if they had their acts together to work in the best interests of the kids, and if the kid was well adjusted, no reason not to go ahead if all else checked out.
This last bit is important. Honestly, most people will have baggage. The question is, is it carry on, or seriously overweight? If the latter, sorry, the shidduch’s a no-go, however old the kids are. If the child’s well adjusted, but the family matzav is complicated, then an older single can decide, with our input, how much she can handle and if this is something worth pursuing.
No one should say that you should limit yourself to someone with an identical background. BUT it is very possible that your experience has given you extra depth and you might do well with someone who has his own story that transformed him. So don’t think right away that if someone’s suggesting someone for you who’s a bit off the beaten track that you’re both damaged goods.
OTOH, it is entirely possible for you to marry someone from a conventional background and stable family. I know for a fact that these shidduchim can happen. And BTW, we all know of so-called “nuclear” families that are downright nucular and ready to ex- or implode at anytime.
I think you’re getting a lot of good input here and food for thought. Take your time digesting!