JDL’s 1000 South Clark (above) and Fifield’s E2 (below), both in Chicago, have crossover appeal to two generations of renters.

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It’s been a truism for some time that renting is a young person’s game—or, more properly, preferred mode of living. And while twenty-somethings move out of their parents’ houses and into apartments, the parents eventually face empty nest syndrome, downsize out of those homes and move into retirement communities in warmer climes. At least, that’s how the conventional wisdom has imagined the sequence of events over the years.