I moved to San Francisco in the summer of 2000, the beginning of the end of the last tech boom. After telling me I was hired, my first boss broke the bad news: She wanted me to start in a month’s time, and finding an apartment in the city so quickly—while I was stuck in college across the country—was going to be hell.

When I asked my new boss if she had any tips for navigating the apartment market, she told me that there was only really one way to do it. “It’s called Craigslist,” she said, and then she spelled the URL out for me. I remember thinking it was a funny name; who was this Craig? “It’s really a great site,” she assured me. And she was right. Over the next few weeks, I scoured Craigslist hourly, jumping on any leads that seemed like they could work. Eventually, in the nick of time, I found something.

But even then, the site seemed as maddening as it was magical. Sure, it was nice to have a dynamic, searchable index of all the apartment and roommate ads in the city; Craigslist was unquestionably better than the newspaper classifieds it replaced.

But there were so many shortcomings. Craigslist didn’t have a map; you could only see ads as a list, which is the least intuitive way to look for apartments. It had no way of telling you about where the apartment was located—sure, it listed the neighborhood, but San Francisco’s neighborhoods vary widely in culture and climate, and Craigslist offered no help in navigating them. Why not give me details about an area’s crime stats, walkability, or distance from public transportation? Why not tell me how a listed rental price stacks up to other places in the neighborhood? Also, can you please tell me something about the person offering this apartment? Is he a good landlord? Is he a good roommate? How many times has he posted similar listings?

A lot of these features were beyond the capabilities of any site at the time. But anyone who’d used Craigslist in 2000 and felt the pain I did would have expected, as I did, that Craig and his team would add these necessary features over time. Craigslist was just too good not to get better. But then, amazingly, it didn’t. Seventeen years after its founding, as the rest of the Web became a bustling, social wonderland, Craigslist remains ossified in the mid-90s. Others have pointed this out before (read Gary Wolf’s fascinating 2009 Wired profile of Craig Newmark) and there have been several attempts to take Craigslist on, but Craigslist has managed to stomp them all. That’s because Craigslist is mostly free and uninterested in making money (it rakes in a pretty penny from the few listings it charges for), and it has repeatedly stopped clever young companies from scraping its data—which makes competing with it all but futile.

But I suspect the tide might be turning. Thanks to Facebook’s IPO, Twitter’s decision to stay in the city, and the rise of dozens of start-ups, San Francisco’s real estate market is once again booming. To get an idea of how difficult it is to find an apartment in San Francisco right now, read this post that Jason Evanish, product manager at KISSMetrics and new SF resident, put up over the weekend. Evanish offers a 10-step guide for finding a place, and he cautions that “that apartment searching here is a ‘full contact sport.’”

Among his main ideas: Ditch Craigslist. I bet he’s not alone. The people who are flooding SF during this new boom—Facebook millionaires, impatient engineers, sales and marketing folks who’ve given up their laptops for iPads—aren’t the sort who are willing to tolerate a sub-par Web experience. They all understand that Craigslist could offer much, much more. And they’re happy to quit it for something that does.

How much better might Craigslist get? One great model is Lovely, an apartment search site that launched last year, which adds dozens of features that Craig forgot about. Lovely has a sensible map-based interface, it lets you narrow down your findings by price and size, it shows you how fresh each listing is, how many other people have viewed it, and it helps you track which places you’ve contacted and heard back from. Best of all, it offers ways to help you stand out to landlords. For instance, the site will build you a “renter resume” to take to a showing. If you like the joint, just hand in your professional-looking CV and watch the landlord swoon.

But Lovely—like PadMapper and others in this space—is still missing other features I’d love to see. It would be relatively easy, for example, to superimpose walkability and crime scores over neighborhoods. These sites are also screaming for better social-networking integration. When you click on an apartment, you should be able to see if you have friends who live nearby—you can ask them about the neighborhood—or if there are bars and restaurants that your friends often check into. It would be great for renters and landlords to see profiles of one another beforehand, too, and for previous renters to provide testimonials and reviews of apartments, Airbnb-style.

But the one problem facing all of these would-be Craigslist killers is that, as soon as they become enough of a threat, Craigslist can easily crush them like a bug. Lovely, Padmapper and others scrape many of their listings from Craigslist. In the past, Craigslist shut down Jeff Atwood’s all-city search tool as well as Listpic, which allowed you to browse Craigslist by pictures instead of text. Each time, the classified giant cited violations of Craigslist’s terms of use. At the moment Craigslist seem to be tolerating the upstarts, but for how long?

The more important problem is that by offering an abundance of free advertising space, Craigslist has created a killer price that any feature-rich start-up will have a hard time matching. Usually, this is to be commended in the market: It’s great when people offer stuff for as low a price as possible. But when low prices hold up progress—when the low-price leader refuses to improve its services, and effectively prevents anyone else from doing so—the free model becomes a noose on the entire industry. I wish Lovely lots of luck. I really hope that in this new tech boom, someone finds a way to cut the rope.