If you don’t try, you’ll never know what’s possible. That’s the philosophy Tracy Crawford adopted when she set out to buy and renovate her dream home. For seven years, Ms. Crawford had lived in an adequate house in Pittsfield, Mass., with her husband, Craig Crawford, and children, Riley, now 18, and Maggie, 14. But whenever they drove into the city center, they passed a 1938 house that was impressively large — 5,500 square feet, it turned out — on a bucolic six-acre property with a barn. “I was always like, ‘Oh, there’s my dream house,’” said Ms. Crawford, 54, the…