There are too many replies to multi-quote so Ill just make a few comments to let you all know I am reading the responses and I truly do appreciate all the feedback.
This has gone into a bit of a different direction. I was hoping for more posts like the ones who have experienced a similar situation and have some feedback to share. It has gotten more into questioning my relationship and that was not my intent.
First, for all technical purposes, we are married now. We live together, share expenses (yes she chips in but her main goal now is to pay off her debt which is almost done). She is very aware of how my divorce went and she lives it every day with my ex-wife. As a small digression, I want to say that in my opinion, the institute of marriage is baffling to me. Nobody goes into with the expectation that it will end and everyone states to God, to friends and to family that it will last forever, yet 50% of the time it ends. I personally believe that when you make that kind of commitment, you honor it and you try to make it work. But in this country, all you need to do is say, Im bored with you and you can move on. So the folks who say, if you are thinking about it ending, you shouldnt be getting married are kidding themselves because I can think whatever I want, I cant control it. My ex wife did nothing to try to keep our commitment and family together - not even one session with a marriage counselor. After 20+ years together, she literally walked out leaving me with the house and kids. The problem with a marriage is that once it ends, the state/courts gets involved and it can get ugly.
As I mentioned in my last post, the kid issue is the bigger concern and has the biggest implications to the current and future family dynamic, financial, stress, etc. If we do not have kids and only get married, a pre-nupt would probably suffice.
Honestly (and no, I am not kidding myself, here), neither of these 2 items are hills to die on for me or her. We have excellent open communication ~ a lesson learned the hard way from my first marriage. We talk about this all the time and we both have been on the fence about both items especially the having kids because we both understand the variables. Up to last week, I would say we were square on the fence at 50/50. This week, I am starting to lean one way and she is starting to lean the other way. My feelings of nervousness about being older, financially supporting, and the impact to the family dynamic, do not dimension how awesome it would be to get a chance to start over with a new person. I consider myself lucky to have that chance. Our love for each other transcends both of these items and we will work together to make sure we are both happy. But to everyones point, if we truly cannot come up with an arrangement that makes us both happy, we would have no choice but to break it off. I dont see it coming to that.