Twice.
In 1992 shortly after our second child was born. Needed a 4th bedroom, and wanted a 3 car garage. Looked at 30 houses and found that getting those two things was going to cost $100,000 more than our home was worth, not including moving expenses. Adding a bedroom on our house cost $24,000, and we gave up on moving up from a two car garage to a three car garage.
In 2013 after my mom passed away. We could have moved into her house and sold ours, stayed in ours and sold hers, sell both and move somewhere else, or keep both and rent the other out. Decided to sell mom's house and use some of the money to remodel our house.
Been in this house 41 years. Hope to break my mom's record of 53 years in the house she and my dad bought when I was 3.