In a recent survey by Trulia, the #1 homeowner regret was not purchasing a bigger home. Here in Steamboat, it’s common for a second home buyer to purchase a smaller condo then realize they don’t have space to host friends and family. A few years later, they sell the condo and move up to a townhome with more bedrooms and space.
Other regrets of homeowners were: not investing more in remodeling and renovations when they purchased their home, not putting more money down at the time of purchase, and not buying closer to work so they had a shorter commute. (#3 doesn’t apply here in Steamboat Springs because everything is less than 10 minutes away unless you live out of town.)
Here’s the WSJ video with the full interview: