Picture two mountain properties with nearly identical listing photos. Both have a stone fireplace, a balcony, a comfortable kitchen, and enough room for a long weekend with the family.

One is a straightforward second-home purchase. The other comes with different ownership responsibilities, financing questions, or rental restrictions that …

We’ve worked with parents who decided that rather than pay rent for several years, they wanted to explore buying a condo or townhome, letting their student live there and—if the property and association rules allow it—having roommates help offset some of the cost.

Then, when graduation comes around, …