Where...oh where...to retire?

A good question that a lot of us "baby boomers" are starting to think about!

A good friend, Carol Rockwood, decided to retire....so they soldl their business and moved "lock, stock and barrell" to the deserts of Arizona from Massachussetts. They had only visited Phoenix during the "winter months" so they had NO IDEA what the weather would be like in the summer time! After a summer's experience with 124 degree temps, they now go to mountainous Flagstaff for cooler, breathable air....
I don't want to make their mistake! 

Seems like there are a lot of questions to answer when this subject comes up in conversation....

1. What do we want to do when we retire? Work? Fish? Volunteer? Travel? Lay on the beach?
2. Where do we want to live...one place, two places, or more?
3. When do we want to make the investment in the "place/places?"
4. How much longer do we want to work?
5. How much money do we have to have to survive old age comfortably?
6. What do we do about medical expenses and life insurance?
7. What kind of amenities do we want.....weather? town vs country? mountains vs beach?

Lots of questions need answered....