Even before he became a financial planner, David Rosell knew something about creative life planning. While still in high school in Saratoga Springs, N.Y., he resurfaced driveways. When he sold the business at age 30, he netted $200,000, enough seed money to fund the next phase of his life.

In 2000, he and his wife launched a hunt for the perfect place to settle down. Like many other winter sports enthusiasts, as well as retirees, they chose Bend, Ore., a community on the lip of the Cascade Range.

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