The one bright spot for apartment hunters over the past decade has been the emergence of online aggregators like Zillow, Trulia, and StreetEasy, which scrape property listings from around the web and organize them in one place. "StreetEasy, especially, has been killing it," says Curbed’s Steele. "It’s a real godsend if you’re looking to find clean, reliable property listings." For a small fee, StreetEasy will even show apartment seekers how much an apartment and comparable properties have rented for in the past. "Comps are an invaluable tool for consumers who want to get the best price." says Steele. "The problem is, once you find a place you like, these search sites just pass you off to a random broker, with no guarantee of honest service."

Urban Compass aims to marry this kind of search technology with its own in-house brokerage force. Allon’s first search engine, Orion, scoured the enormity of the world wide web, and is now part of Google’s core search algorithms. His second company, Julpan, kept tabs on the torrent of real-time messages coursing through social networks, and is now part of Twitter's search. By comparison, the apartment rental market in New York City five boroughs, with a little over two million total units and just a few hundred new listings per day, seems like a rather small and slowly shifting data set.

The company has also employed a small army of agents over the last six months, each equipped with a brand new iPhone, to pound the pavement, verifying apartments in person, snapping photos, and marking locations with geotags. It currently has 30 brokers, which it calls neighborhood specialists, and plans to hire 100 by the end of the year. "We are going to launch with an almost comprehensive database of apartments in Manhattan, from open listings to exclusives," says Allon.

"We’re not just building a brokerage. Real estate is just the first application."

Despite Allon’s ambitions, getting every apartment in the system may not be possible. New York, unlike almost every other state in the nation, doesn’t require all available properties to be be publicly listed through what is known as a multiple listing service, or MLS. "It’s anti-competitive and at some point it will get struck down, but right now, that’s the lay of the land, and it makes it a lot harder to disrupt incumbent players who have built up relationships with landlords over decades," says Steele.

So while there is a ton of pain in the market for consumers, the real power for change lies with the sellers, the landlords, who have very little incentive to change. "Why should 80-year-old Donna, who happens to own a couple dozen great properties, learn to work with some complex new technology?" asks Steele. "Her apartments have been renting just fine. She’ll keep right on working with the brokers she knows, and they will do business as usual."

In fact, the antiquated nature of the rental market, with some landlords still faxing new listings in to their favorite brokers, is something property owners may want to protect. "The idea of having more transparency is not something landlords are necessarily going to be interested in," says RealDirect’s Doug Person. "If they rented an apartment on the third floor last week for $2,700 a month, but the market has tightened, and now they want to rent same apartment on the fifth floor for $3,500, that is not something they want buyers to be aware of."