Caroline, a friend Gato had met through Lillian, needed advice concerning moving from Milwaukee to New York. Gato wondered why, since she lived in the South Ward, a neighborhood of particular small-city magic.

Gato had been asked to contribute writing about the Big Apple to a strange travel-like book called “A White Collar Fugitive’s Guide to America’s Best Cities: On the Lam and Loving’ It.” He figured he might as well try out some of his research on Caroline.

Caroline, Gato and Lillian met at Vin, the wine bar with the interior inspired by architect David Rockefeller, on Madison’s Capitol Square. As the first glass of Tawny Port was poured, Caroline revealed — as usual — a break-up got her ball rolling. “But the most difficult break-up is leaving Milwaukee — but I need a more dynamic place, aggressive,” she said with evocative gestures. “I just want to be positively certain. ”

Absolute certainty is the absent father of disappointment, and if listened to repeatedly, he’ll become the grandfather of failure.

Doing things in terms of “certain,” overlooks serendipity that sparkles after 70 percent good planning and 30 percent being open to possibilities. Steps involving risk also move one’s self-concept beyond the present, inspiring feelings one can climb bigger mountains. “Put it this way,” Gato offered, “Sinatra’s ‘New York, New York’ wasn’t written by some 28-year-old pudgy, living in his Mom’s Cleveland basement.”

There’s a rule Gato learned from University of Pennsylvania professor Richard Ingersol: proximity has a lot to do with the prestige of an institution. To that effect, even Harvard has a minor prestige problem right in Boston because lots of folks there know someone admitted by legacy with brains of soup-in-a-bread bowl. On the side of UW Madison graduates, the degree has more prestige in New York than it does where the cows come home. (Mad grads also struggle with the Marquette ol’ boys network in Brewtown).

Caroline also wanted to live in an ethnically diverse neighborhood. “Especially since my dad’s Jewish and my mom’s Nicaraguan, but from the African area near Belize,” she said. “Some cities just don’t get excited about fusion cuisine like me.”

That in mind, Manhattan is fantastic but the real New York stories are in the boroughs and for the most part, less-expensive rents. By borough, Gato brings tips on neighborhoods that feature one and two bedrooms at rents between $600 and $1200.

Rumor has it that everything is more expensive in New York. Rent is the only factor where that stands consistently true. Otherwise, Gato invoked the London of old as described in Adam Smith’s “Wealth of Nations” — what one can pay for groceries and even a regular watering hole, runs the gamut.

Gato assured Caroline that pay is significantly better, and if anyone played their cards right, they could realize the old wives tale of spending only 25 percent of your monthly income on rent.

That said, here’s the magic, observable equation for not-worth-it: first, add hipsters with semi-punk rock hairstyles, then drug dealers on BMX bikes, subtract good grocery stores and subtract green space and you get — tadah! — overpriced apartments. Hence, places like Williamsburg/Greenpoint in Brooklyn, and even Jersey City, are not the bargain they’re rumored to be.

Surviving in a new city for the first year, everyone needs five basics: a good grocery store, green space, a friendly diner, a cheap local bar and late-night laundry.

Brooklyn is the first borough to really gentrify, so to find bargains, go further out. Bensonhurst–Bay Ridge are almost to Coney Island and have a smattering of quiet grad-student twenty-somethings. Weekly local papers, the Bensonhurst and Bay Ridge news, have apartment listings, even two bedrooms, between $800 and $1000.

Bensonhurst, under the el tracks, has Manhattan flavor plus better Italian restaurants. It’s almost Biblical, you really haven’t had wood-oven pizza until you’ve had it on 86th in the ‘Hurst.

To use the kind language of avoidance, Bay Ridge is far more accepting with it’s mélange of Orthodox Jewish, Dominican and Middle Eastern for starters. At the same time, Bensonhurst has become a beachhead for Central American migrants, losing some of the f-word, gold chain Machismo

Love Brooklyn and want to find places before they go on the market? Hang out on Coney Island in the summer; buy a dollah beer; get to know people. “Blending yourself in means you can tap into the menschlichkeit of any city’s word-of-mouth economy,” Lillian added.

“So what about New York’s black neighborhoods?” Caroline asked. Gato completely ignored the fact that Lillian had interrupted with a “Don’t you mean African-American?” and related that Flatbush in Brooklyn and Parkchester — off the 6 line in the Bronx, 40 minutes from Astor Place in Manhattan — are two of the best places for those looking to live in a vibrant, mixed-income neighborhood.

Parkchester is a co-op community where along the forest of a main drag, Metropolitan Avenue, one can find everything including a Macy’s with one of the best back-of-store bargain bins in the city.

Seventies films, J-Lo and the New York Yankees have given the Boogie Down a bad rap,” Lillian said. While this isn’t Gato’s opinion, the Bronx is cheaper than Brooklyn, and it’s trains run faster into Manhattan,

“There’s also … there’s also Jersey,” Gato said, holding his breath.

Caroline didn’t wince so Gato recommended Jersey ‘burbs’ that have a small-town-in-a-city feel.

In West New York, high on the Hudson River Palisades, a two-bedroom share with a view of Manhattan will put you back $600 to $700 a month. For Chicago-burbanites, West New York also features an inexpensive golf course.

Harrison, only 20 minutes into Manhattan, is a town that feels like Green Lake, Wis., and Gato can’t figure out why it hasn’t been overrun by Wall Street types. One-bedrooms for $500 to $600 are pretty much the norm.

“So what about decent jobs for chicks in a bootstrapping situation?” Caroline asked. Gato recommended a great New York networking secret — becoming a producer in the executive conference industry.

At that moment, Gato had to take a phone call. Next week, he’ll have Sexy Job recommendations, networking and the best placement agency resources.