We run through my residential desires: something in a fun area and close to the el, preferably with convenient parking for my roommate (who is spending the summer in Montana and therefore cannot be with us). He scrolls down the available listings in the $800 to $1,150 range, clicking only on those $1,000 or above. I didn't ask him to show the cheaper ones and Steve, as he later tells me, works on a commission from the month's rent the company receives only if it makes the sale. He gushes at a listing advertising a Jacuzzi, telling me that the listing on North Whipple and Logan "looks huge but won't be too nice at all," kindly drawing dots on a map to show me where each building is and how long it will take me to walk to the train. We decide to visit an apartment on West Crystal in Wicker Park ($1,150), one on North Wolcott in Ukrainian Village ($1,000), the one on North Whipple in Logan Square ($1,150) and another on Shakespeare in Logan Square ($1,000).

While bopping from apartment to apartment Steve shares stories about his first bottle of Cristal champagne, his archaeological adventures in Greece, and his trip to Guatemala on a California unemployment check. I also give him advice on picking up his girlfriend at the airport, and yes, I learn a bit about apartments and landlords. Steve is a Wicker Park resident and we chat about the neighborhood's recent rise in popularity and rent. His customary response to potential renters' inquiries about his "Real World" sitings is, "No, I never saw them—but I did see my rent go up."

Our first stop is on Wolcott, an adorable red brick building on a tree-lined street. The apartment is still furnished, featuring, inexplicably, a third mattress on the kitchen floor, and an aggressive tabby cat. Steve points out a copy of the Trivial Pursuit Genius IV Edition as well as the Periodical Table of Elements hanging on the wall. I point out the extremely cramped nature of the bedrooms, though the high ceilings and central air are nice.

As we enter the apartment on Crystal through a maroon door that's the exact shade of his silk shirt, Steve sheepishly informs me that his ex-girlfriend has lived there. "I've actually slept in this room," he says. The place has an excellent Wicker Park location, a spacious living area, large windows offering a second-story view of the street, and a pleasant, though slightly decayed back porch. It does not have central air, but then again, most of us don't, and, except for an old-fashioned bathtub/shower that appears slightly hazardous, I kind of want to move in. But I don't tell Steve that, not wanting to taunt him with a false commission.

So we drive on to Shakespeare without any positive reinforcement. As we go, he comments on the area's lack of nighttime activity and fine dining, but also notes the apartment's close proximity to the el. I note the generic cabinets and light fixtures, miniature kitchen, and the upwards view of the sidewalk. By this point it seems that perhaps my lack of enthusiasm has increased Steve's salesmanship. As we headed to the apartment on Whipple, which he had earlier criticized, he drops this one: "Judging from other apartments I've seen from this company for less this should be a real nice place." We enter the apartment to salsa music and paint fumes. The two men sprucing up graciously take a break from painting the entire apartment a cream color to allow our tour. It's huge, with luscious greenery obstructing and enhancing its multiple second-story views. After speaking to the painters in Spanish, which, as I discovered earlier, he learned in kitchens and Guatemala, Steve tells me that the men are not only painting but also re-varnishing the floors. And though this last place is spacious and sitting right on Logan Square, if I had to choose I think I would have braved the shower and taken the Wicker Park space.

After seeing the fourth apartment, we return to the Apartment People headquarters where Steve eschews the hard-sell, simply shaking my hand and handing me his card. Unlike most apartment searches, the afternoon with Steve was actually enjoyable, very low pressure and definitely worth my two-and-a-half hours—if only for the chance to go around with someone who knows which apartments are worthwhile to visit. After all, scoring a sale involves showing desirable units, and he seemed to honestly describe the activities, or lack thereof, in each apartment's vicinity. Not to mention the fact that Steve went out of his way to be entertaining, a definite plus in a small car on a two-hour tour.

Apartment People, 3121 North Broadway, (773)248-8800