When it came time to leave Florida, Harold and Alison Issen put together a list of their preferred destinations. The couple, who grew up on Long Island but didn’t meet until they were living in the Sunshine State, had raised their family in Orlando. As the years went by and their son and daughter grew up, they felt they had outgrown Florida.
“More and more every year, in some ways,” Ms. Issen said.
Houston, Denver and especially Asheville, N.C, were high on their list. They took their first stab at buying in Asheville last year, but arrived a little too late, just as prices there were soaring. On their way back, they learned that their son and daughter-in-law, who live in Chicago, were expecting their first child.
“That just shot Chicago to the top of the list,” Ms. Issen said. “They’re renting, and we’re like, ‘OK, it’s a little risky, but they love it.’”
Mr. Issen, 65, works as a research psychologist for the Navy, and Ms. Issen, 66, is a semiretired mental-health professional. The two set a budget of $350,000, but raised it to $400,000 after their financial advisor emphasized the advantages of getting a mortgage rather than buying in cash.
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The couple hoped to find something in North Chicago, on or near Lake Michigan, or just north, in suburban Evanston. They made their first trip to the area last December, and then another in February.
“It was very intense, and our poor Realtor was fantastic,” Ms. Issen said. “She doesn’t like to show more than three or four homes a day because they all start to blend together, and we’re like, ‘We need to see eight to 10,’ and she did it.”
The ability to be hands-on grandparents wasn’t the only draw. The couple were fans of “The Bob Newhart Show,” the 1970s sitcom set in Chicago. “Newhart would always come home to this nice condo overlooking Lake Michigan,” Mr. Issen said.
In addition to being close to the lake, they wanted a place with at least two bedrooms. Ms. Issen was willing to consider a single-family house, but her husband didn’t want to do yardwork. He did, however, want a place to store his tubas. They also wanted to avoid climbing a lot of stairs, which narrowed their options.
As for the Newhart fantasy, the couple found that many lakeside apartments in their price range were very small and lacked closet space and parking. “So living in a glass-front condo on the lakefront wasn’t the highest priority after all,” Mr. Issen said.
But a few blocks from the water, they could find three- and four-bedroom apartments, their broker, Tedi Smola of @Properties, in Evanston, advised them.
Among their options:
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