When it comes to real estate, I have been lucky, much luckier than a 20-something journalist renting shared spaces with roommates has any right to be.

It began when I arrived as a freshman at the University of Chicago and discovered that my dorm was not the depressing low-rise tower with cinderblock walls and shared bathrooms in the hall that I had braced myself for, something designed by an architect who did dorms when he wasn’t designing prisons. Instead, I was greeted by an historic, if down-at-the-heels, former luxury hotel overlooking Lake Michigan. It had a ballroom, a storied history of mobsters and celebrities, and enormous suites that boasted not only living rooms but also full baths, kitchens and dining rooms. All that was missing was a bellhop.

As first loves often do, the dorm/hotel became the archetype of all that I wanted and expected in a home—beautiful and rambling, abundant in history and friends. It was unreasonable to want it, even more so to expect it, but then, I kept on getting what I wanted. Even more perplexing, it was often through Craiglist.

Over the past 10 years, in Chicago and San Francisco, New York and New Haven, I’ve lived in houses and apartments that featured 12-foot ceilings, bay windows, working fireplaces, closets the size of small rooms, wood paneling, spacious backyards, spiral staircases and in one case, the ridiculously low rent of $250 a month. It was a gracious Chicago coach house behind a decaying mansion, located, by odd coincidence, roughly a five-minute walk from the homes of both Louis Farrakahn and then-Senator Barack Obama.

Not to play Pollyanna, but with the exception of a few hiccups—mice that traveled in packs, bedbugs, some bad roommates and becoming deeply involved in one landlord’s bankruptcy proceedings—I’ve loved almost every place I’ve lived, and nearly all of the people I’ve lived with during the first decade of my adult life. Given that I’ve lived in 10 different places with a total of 66 people, not counting 4 cats and 4 dogs, that’s not a cheap sentiment. (A disclaimer: I have a high tolerance for leaking ceilings, broken boilers and other people’s messes.)

So I approached my most recent apartment hunt, a return to New York after two years in New Haven, with a ridiculous amount of optimism. But this brightness of spirit was tinged with considerable anxiety. I knew that the streak had gone on for too long—luck is nothing if not fickle. I was definitely due for something overpriced and nondescript.

I had expected cramped and dumpy when I first moved to New York in 2009, but my confidence this time around was bolstered by the fact that I found bright, airy and relatively inexpensive in West Harlem. Complicating matters, I was moving back to New York to work as a real estate reporter for The Observer, so for shame’s sake, I had to find an apartment that was, if not ideal, at least not obviously terrible. Would luck be a lady this time around, or a bitch?

To kick off the hunt, I turned to my old friend Craig.

A successful Craigslist hunt must be conducted with zeal bordering on obsession (fortunately I’m naturally obsessive), and for nearly a month there was scarcely a time when Craigslist was not open on my computer, hardly an hour when I was not responding swiftly to every post I deemed promising, vaguely promising or, in moments of desperation, potentially promising. I did my best to avoid the deeply depressing.

These included a shared apartment on the Upper West Side with the proviso, dropped like an afterthought at the bottom of a paragraph, “Note: room does not have an outdoor-facing window.” (Later, after viewing several other essentially windowless rooms—and no, a transom is not a window—I would admire the honesty of that particular post).

I also avoided rooms that were described as “on the smaller side,” and/or “good for someone who doesn’t have much stuff,” and any listing that described the size of a room, or rather, avoided describing the size of a room by listing the furniture that could fit inside of it. These posts brightly noted that the room was capable of holding a full bed and a small nightstand, possibly even a bureau. I have seen many small rooms, but none so miniscule that they could not accommodate a full bed and a nightstand. One of the downsides to living in, and growing accustomed to, large spaces is that one becomes a bit of a hoarder. Moving to a bad apartment would be bad enough, having to give up my worldly possessions would be even worse.

FINALLY, I AVOIDED ANY LISTING WRITTEN ALL IN CAPS. This was a much larger number than I would have expected.

This left many posts for eminently livable, definitely worth a look, possibly even undiscovered gems of apartments. Because non-smoking, pet-free professional women in their mid-20s—bland though they may sound—are a very popular bunch among the room-4-share crowd, I was invited to see many of the apartments I inquired about.

My optimism was, almost immediately, dislodged. Over three weekends, I saw 24 different apartments, all of them shared. I saw many rooms without windows—prevalent, but a housing code violation—a few rooms that involved walking through other people’s rooms to get to the rest of the apartment‚—which sounds almost charming when it’s called a “shotgun share”—and one bedroom—basement, airshaft window, Williamsburg, $925—that required taking the leaseholder’s growling pooch to doggy daycare in the mornings. It’s not that these were impossible situations, really, but what irked me is that there was no acknowledgement of their inferiority. In fact, most were among the more expensive places I saw.

The search started well. As I stood outside the door of the first of six apartments I had scheduled to visit one unseasonably warm day in late February, the sun broke through the clouds in an encouraging way. The apartment—a 4-bedroom on the Upper East Side—was promising, if not a perfect match. The roommates seemed genuinely nice and the space was pleasant: good light, a full-size kitchen, maybe not the trendiest location, but a very, very nice one. The room was small, but it had a large window and an actual closet. I would soon understand the rarity of such amenities, but at the time, I simply wrote down the room’s measurements and snapped a few pictures. As it was the first place I saw, I had no reason to assume that there would not be other, possibly better, apartments out there. I rather smugly filed it in the “maybe” pile.

By the second stop—a significantly more expensive apartment in Williamsburg—this bit of beginner’s luck was already slipping away.

I arrived a little before noon to find an apartment thick with pot smoke. The roommates, who appeared to wholeheartedly embrace the Williamsburg lifestyle, extending to the inelegantly and cheaply executed loft conversion where they lived, said they worked in finance. One hazily narrated a tour of the apartment, starting with a partially furnished living room (it came as a surprise to learn that the apartment had been occupied for the past four years) and ending with the medium-sized bedroom available for rent. The “great light,” mentioned in the Craigslist description of the room had apparently referred to the light situation elsewhere in the apartment, as the room did not have a window. Or perhaps it referred to the fact that the room did, in fact, have a light fixture.

The next few weeks could be described as a downward slide, with my expectations crashing like a foot through a rotted floorboard—an indignity I was spared, though it would not have surprised me at this point, at an asking rent of $1,200-a-month, no less. I met a lot of very pleasant people with terrible apartments, or terrible rooms for rent, or at least terribly overpriced ones. I thought longingly and often of that West Harlem apartment. I even went to look at another unit in the same building, but like so many others, it didn’t work out.

There were several strong contenders with equally strong downsides: the owner planned to put the house on the market in August. The roommates were only renting the large, lovely room on the first floor in combination with a small, windowless room in the basement. A communal loft in Williamsburg had glimpses of such brilliant whimsy, even to my hipster-hardened heart—a bathroom with walls housing hundreds of cassette tapes and a built in radio nook, for musical showers!—that I spent the rest of the day trying to talk myself into the unfinished walls, ceilings, stacks of construction materials, and the high price I would pay to live amid such precious detritus.

I also saw places that I could live in, or could convince myself to live in if I reached the level of exhaustion and desperation necessary for such personal persuasion. But like a brat with indulgent parents, I’d always been rewarded for holding out before. I was determined to keep looking. At least until the middle of March, when the real desperation began to set in.

I knew I was being unreasonable, but because so many of my best friendships and experiences and most everything that has mattered since I went to college has been so deeply entangled with the places I’ve lived, it’s hard for me to look at an apartment and just see an apartment.

After one particularly bad day of viewings, I got back to my house in New Haven (sprawling, bedroom the size of a studio apartment, though, yes, it is in New Haven). It was a little after midnight, I was exhausted and so despondent that my roommates, who are generally not prone to physical displays of affection, offered hugs.

“It’s only a few days until March,” one murmured comfortingly. “You’re getting the month’s dregs.”

The explanation was reasonable and surprisingly comforting. But unable to sleep, I spent the next few hours combing Craigslist, reading housing ads that I’d already read a half-dozen times before and chastising myself for the slow, non-committal follow-ups I had sent to the handful of decent places I’d seen in the past few weeks (probably how I’d lost apartment No. 1).

None had won me over, but really, they’d been good enough. They were the kinds of places that I would have lived if I hadn’t been so spoiled by my previous good fortune, if I didn’t feel that taking an apartment that was “good enough” would constitute a defeat. If, when it came to real estate, I didn’t secretly believe in, and hold out for that sentimental old saw—love at first sight—that I did not believe of romance, or really, anything else.

The end of March brought with it a tide of cheaper, better, more attractive postings, including a light-saturated bedroom in Bed-Stuy, close to the border of Clinton Hill. It was located in a large shared house, the kind I’d been looking for, with a huge backyard and a pressed-tin ceiling in the kitchen. Moreover, there was something happy about the tone of the post that buoyed my spirits.

Walking to the open house that weekend, the building caught me by surprise—a free-standing wood frame beauty with a mansard roof and a porch swing lodged in a block of brownstones. Behind an iron gate, chickens roamed in the front yard (I immediately coveted the absurdity that 4 chickens would lend to my ongoing roommate count, even as I worried that Brooklyn chickens, and even moving to Brooklyn at all, were too au courant).

It felt like providence, but I was not the only crusader. The place was packed with other eager would-be boarders. As I walked around the house, I felt a crush taking hold. But besting the other suitors posed its own challenges—how to write a follow-up email that was earnest and persuasive without being overly ardent or creepy?

The owner, who documented the house’s history in a 2009 New York Times article, told me that the house had hosted lavish parties written up in the society pages during its early years, later becoming an underground R&B bar, then the center of a sizable crack dealing operation whose end was precipitated by a series of murders, and finally, a house that now holds 13 people. Also, it sat over a mysterious hidden tunnel the provenance of which remains unknown.

As she spoke, I felt woozy and excited and, all-at-once, very lucky. Maybe even the first stirrings of love. I moved in last week.

kvelsey@observer.com

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