Guys - great discussion.
1. Practical point on managing income and Health Care options.
For folks considering medical care options if they retire with a gap in health insurance: take a look at ObamaCare (this assumes you have enough saved in a capital gains situation to pay for a good portion of your yearly spending). I had looked into this somewhat a few years ago but here are the basics (looks like TJ or Warp would know about some of this):
--Long term capital gains are taxed at 0 until you hit a decent amount of income (75,000ish?). Keep in mind, to have that high of a gain, you are pocketing much more than 75,000. We live in an expensive area but haven't really raised our standard of living too much and feel like we live a relatively luxurious life (albeit with a 10 year old CRV that I love). Our commit/needs side of budget is below that number (admittedly I am lucky enough to have a very generous deal on health insurance).
---401k/403b plans are ordinary income (as are pensions), which is taxed at a much higher rate. It is good to have diversity of income streams if one can (always the hard part and I am not saying I am an expert!)
--I can't remember which tax number ObamaCare uses (Adjusted Gross Income)? but the subsidies are pretty good until the AGI gets somewhat high - perhaps around a similar income level. Again, if you have cap gains, you are pocketing more than the amount than listed on your tax return (say you invested 75,000, sell the capital item for 150,000, you have 150,000 and your cap gain is 75,000).
---I have seen stories that ObamaCare doesn't always have great choices.
---Keep in mind, THIS HAS NOTHING TO DO WITH AGE - just your income (you'll have to google which type of income number they look at.
These practical points help facilitate living the dream.
I am a bit away from the dream part, and may not have as many models as warp, but I was born a planner. With luck and living below means, we will have good options by the times the kids are out of HS.
2. My dream - TBD
Not exactly sure what our dream looks like. I like the beach and the mountains. We are somewhat close to family geographically, but with my kids' ages (4th and 1st grade), life doesn't leave a ton of time to see family, but it is nice we can see them fairly frequently albeit socially distantly.
I could see splitting our time. If I retire early enough that I still can learn skills, would love to figure out the whole ski van thing - who knows by then it is extremely likely it could be electric and I wouldn't have the environmental guilt of a gas guzzling ski van . . . . Vermont electricity is expensive but ridiculously clean; NY electricity is cleaner than most states. In WV, you are cleaner to buy from a pump than plug in.