Somewhere between the first school tour and the second home office installation, something shifts. The Litchfield County property that started as a weekend escape becomes something harder to categorize. The commute gets mapped. The grocery run gets optimized. The guest room gets a pullout sofa and a standing desk. At that point, calling it a second home is technically accurate and practically misleading. Bill Melnick of Elyse Harney Real Estate sees this buyer regularly, often from the first phone call. “When you start the search, buyers lay out their requirements and how they’re going to use the house,” he said....