Four years ago, when Judy Cruz decided to try to sell her house on her own, it couldn’t have been easier. She struck up a conversation with a neighbor who said he’d love to buy it from her. Deal done.

But when she decided to sell her Chicago condo this year, it was a different story.

"I tried advertising it online for four months," said Cruz, who explained that posting free classifieds on Craigslist were the sum of her efforts.

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