Our family owned a cottage for 12 years. Our kids were little and we used it a lot, four seasons a year. Then, as happens, our kids grew up. They started going to camp in summer and had hockey or swimming or other activities in the other seasons. By the end, I was going up by myself to cut the grass in summer and get the snow off the roof in winter. We sold out more than twenty years ago. Do we miss it? Sure. The sunsets over the lake, the joy of jumping into the cool water, the pure pleasure of canoeing on a windless day. Can’t beat it. But things have changed. We paid less than $100,000 for our place. Now, the same property would likely go for close to $1 million. Would it still make sense to buy? Here is some advice I gave to a client who asked us just this question.