Joe - The planning and questions here have begun as I am a few years behind you with the girls, college, weddings etc. But I can offer a few suggestions. First, try to decide and agree upon the where(s) of retirement. You know (I think) about the recent mountain house acquisition, and we've planned that to be the 2 -3 season retirement home. We've already decided to launch the RR home when the girls head off to college, as we don't need nor want the drain that a house this size requires. Don't get me wrong, I love my house, but at now 20+ years old, the upkeep is constant and costly to keep the home sufficently updated to the neighborhood and marketable. A smaller townhome or condo in town will be the other home. Just not that hung up on a big home.
As to stopping work, no just doing what I want, P/T teaching, charity work, helping one of our Charlotte LBS with business planning (I've been asked already) would all be potentially in the cards. Doing what makes me feel good, not just to provide a living.
Other hobbies I've picked up and put aside along the way could keep me plenty busy. That's the least of my worries.
Financially, as others have indicated, I believe you need to focus on the expense side of the ledger. Money is easy to spend, hard to save, and markets and unforseen circumstances have a way of biting you in the tail. Perhaps finding a fee-based financial planner who can look at your present situation (i.e.- insurance, savings, investments, available health insurance options upon retirement, personal "balance sheet", etc) would be a worthwhile investment. That way you pay him for the work he does, not get drained by ongoing commission for "managing" your financial affairs. I'm sure you have the ability to mange those things on your own, once you get some comfort and clarity
That's about as far as I am in the process, as I'm likely 5-7 years behind you (God willin' & the creeks don't rise). I'm envious, Good Luck!!!