Question: 

When is the best time to sell my home and move into a retirement complex? My wife and I are at odds with this question. We are in our 70s and are very healthy. I say we stay, and she believes it is time for us to move. Some of her friends have made the move already. All I see is apartment living and old people, yet she sees freedom and security. Would you please weigh in?

Answer:

Yours is a loaded question without a simple answer.  I see both sides of the argument. She sounds like the planner in your relationship, thinking ahead for the both of you. You are likely comfortable with the way it has been in your familiar surroundings, privacy, yard, garage, etc.

Let us walk through the decision-making process. 

You want to know when the best time to sell your home and move into a different situation is. The best time, financially, to sell a house is when the housing market is strong and buyers are plentiful. You can figure out quickly with a little research when it is a balanced, buyer's or seller's market. It is also good to sell when your house is looking well-kept and fresh.
 
Perhaps you are of the opinion that you will stay in your home until they "carry you out," and you do not care what the value is. You may not care, but your wife may, especially if she outlives you. I say living in your home is just fine as long as you keep it well maintained and updated and your yard well kept. If you cannot do it yourself, you should be willing to hire others to maintain it. You must also be mentally able to manage those helping you stay in your home unless you have children nearby who are willing to do it for you. After you take into consideration those factors, you are ready to make a decision with your wife about where to live and when.
 
Retirement communities are good for some and not as good for others. There is no right or wrong.  It is important to find out what your wife is seeking and work together for a solution, as you have done throughout your married life. I have full confidence you can find a situation that works best for both of you.

I wish you well.