Vacation-home owners get e-pay, tax tools

Future-Proof: Navigate Threats, Seize Opportunities at ICNY 2018 | Jan 22-26 at the Marriott Marquis, Times Square, New York

An old friend of mine who owns and operates a small development company showed up in town for a weekend event. We blocked out some time to revisit the old days, and what was next for his living and work future. Like me, his four children had grown and gone. "If I were to do it again," Vince said, "I probably would not have focused so much on commercial buildings. They are difficult to cash-flow because of tenant demands and tenant turnover. They all expect so much in improvements now when they move in. I probably would have bought some nice vacation properties and rented them out. Maybe even moved into one." The vacation rental industry continues to thrive. More and more owners are operating small vacation-home businesses, especially in retirement. They are finding that even in a down economy, families often find a way to get away.The "staycation" philosophy rarely lasts longer than one year; people tend to invest in family vacations and reunio...