I like the bottom's up approach. But things and situations change realize. There is divorce, death, and well unexpected kids. So nothing is set in stone. Just cause you buy a house with plans to stay there or sell nothing is set in stone.
Tell that to my neighbor's they were on the 5 year plan to sell their monster home. But then they accidentally had a baby when she thought it was um menopause and so instead they are now staying put because they want to raise their child in the bigger home and better school district instead of downsizing. Oh well. too bad their older kids were all out of the house in the 5 years plan. Now they get to keep their bedrooms.
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