Tunder01,
If your question was simply "Am I to Old", then the answer would be a resounding NO.
However as you have pointed out, your question is somewhat different.
"Or, do I ante up my savings and my life as it is right now, and go for it?
Do I want to exchange "content" and perhaps "happy", for chance of fulfilling a dream with a risk of loosing a lot, putting me back years. (both eco and socially)"
My friend, we can not answer this. Whatever you choose, your life and your family's life will change by either one of 2 extreme. You will either get a job with agood money and your family will be set up for life PLUS you will have reached your dream. Or you could make your family broke becasue you never got a job. From what I have heard, there is no in-between.
One thing I have learnt is that some pople, even after everything they have spent, will never get an interview, let a lone a job. I'm prepared for that eventuality due to my status. The question is are you prepared for this and can the family survive?