Welcome to Curbed's original series Homeward Bound, in which long-affirmed city dweller and design journalist Karrie Jacobs documents her process as a first-time home builder. Jacobs, a professional observer of the man-made landscape, was the founding editor of Dwell magazine and the author of The Perfect $100,000 House: A Trip Across America and Back in Pursuit of a Place to Call Home (Viking, 2006). This eight-part series is a continuation of Jacobs's pursuit to solve the puzzle of modest, modern, and regional domestic architecture, using a recently-acquired parcel in upstate New York as a first-person case study.

We didn't buy our property in bucolic Andes, New York, because of the barn. My husband Ed and I bought it because the land was uncommonly beautiful, a gently sloping expanse of green with long vistas of the surrounding mountains. It was, we thought, the perfect spot to gently drop a modest, low-slung modern house. But, sometime after we closed on the property in January of 2014, the barn began to loom large.

Sitting on a rise a short distance back from the row of houses that front on Andes' Main Street, the barn was, according to one account I've read, built by a family named Raitt in 1924, although others have suggested that it dates from the late 19th century. The red barn, with a cupola up top, was once a handsome building, but was now clearly in decline, with shredded remains of a tarp covering a roof that had leaked for decades.

We'd explored it, clambering through a low ceilinged area with concrete floors that was once full of cow stalls, pushing away a strand of barbed wire so that we could climb a ladder to the hay loft. The part that really captured our imagination was upstairs, where the space under the pitched roof seemed to go on forever. In our fantasies, the dilapidated dairy barn would eventually be reborn as an arts space. This transformation, we thought, could wait. Maybe we'd tackle it in a couple of years, after we'd built our house.

Then, on Memorial Day last year, we met our neighbors, Mel and June Ruff. At the time, we didn't know that they'd owned the land and the barn until the late 1980s, and that their current house was the original farmhouse. Mel informed us that the barn was in terrible shape, that some of its supporting beams were so rotten that you could poke a pencil through them.

As we stood there, at the foot of the short, rocky drive that leads to our property, we looked up at the barn , a ramshackle box, profoundly weathered and uncommonly lovely. I'd never been crazy about conversions, in which old barns became super-sized houses with ridiculously high ceilings. But we had just realized that this barn required our immediate attention. Maybe, we thought, we could do the necessary work on the barn right away, then insulate the upper portion and turn it into an apartment, while keeping the lower level as a non-weatherized indoor-outdoor space. You know, like something out of Dwell magazine.

So we initiated a series of conversations with contractors. The first one who looked at the barn sent me an email: "It is my opinion that the extensive repairs/reconstruction of the barn would not be a cost effective approach to create a new home.

"The barn had been neglected for many years and the cost of even just stabilizing it will be substantial. I have worked on numerous barn projects and the sheer size of these buildings—even with a modest scope of work—results in sizable construction costs."

But we were not dissuaded. We rented an old farmhouse outside Andes for a couple of week last summer—with a nicely maintained barn featuring an air hockey table and a basketball hoop—and embarked on a research project. Our first move was to walk around the outside of our barn and take a careful look its backside. We were surprised to discover that most of the barn's rear wall, along with the sloping approach to the second floor hay loft, was gone, the hole covered with a tarp. My first thought was that this was something like what happens in depopulated Midwestern cities where thieves steal the bricks off abandoned houses, often removing entire walls. But this was simply one of the mysterious deconstruction projects—weirdly reminiscent of Gordon Matta Clark in nature—embarked on by the eccentric lady from whom we'd bought the property. When we met at the closing, the seller intimated that there had also been a silo that she'd taken down herself.

A friend who lives locally, also the owner of a distressed barn, took a look and said, "It's not as bad as I thought." She pointed out that someone had installed cables in the barn's upper level, a stop-gap measure to keep the structure from falling down the hill. She viewed this as a good sign. She then introduced us to another neighbor, Chelsea art dealer Leo Koenig. His property came with a barn a lot like ours, post-and-beam construction dating from the 1850s. Since 2007, he's been working in tandem with a local contractor, doing a hands-on renovation, replacing rotted beams piece-by-piece and righting the structure by pulling it with a tractor and pushing it with a car jack. The resulting space is dramatic, an M.C Escher drawing come to life, with multiple, oddly-staggered levels linked by stairways.

Leo filled us in on the existential problem of unused barns. Because barns are never winterized, they traditionally require the body heat of farm animals to keep the foundation warm in the winter. Minus the animals, the foundation cracks, and then, devoid of their original purpose, barns fall apart. The non-insulated lower level in my vision was, he assured me, a bad idea. Goodbye, California lifestyle.

In the following days we met with a youngish contractor who was known locally as a "barn whisperer." He took a perfunctory look around, told us we might be able to repair the barn, and gave us an offhand per-square-foot estimate. We did the math and—for a day or two—thought we could save the barn and install an apartment for something in the neighborhood of $300,000. Briefly, we were upbeat.

Then, on the advice of some locals, we contacted a builder named "Steve of Roxbury." He came and looked at the barn more carefully than the previous fellow. My husband, Ed, toured it with him while I stayed outside with the dog. They were in there for a long time.

"Steve took me on a very detailed inspection of the barn," Ed recalls, "basically from top to bottom and he pointed out all the areas where the barn was in distress, including the siding and especially the foundation."

On the other hand, we could bulldoze it for a mere $5,000. We put off that decision until mid-November. So with winter looming, we drove up to Andes and got a demolition permit. When I expressed regret to the town's building inspector, he told me, "You're 20 years too late to save that barn." An excavator arrived in early December, knocked the barn down and buried it on the property. Steve set aside a few choice beams and pieces of siding for future use. June sent me a poignant photo of a piece of heavy equipment interring what was left of the barn.

I have mixed emotions. I thought demolishing the barn was the prudent thing to do, and I was relieved when it was over. But, still, I have regrets. As costly as it would have been to restore it, once it's gone, it's gone. I keep thinking about that green barn in Alabama photographed over the years by William Christenberry. What if someone had gone and torn that down? Wouldn't that have been terrible? In short, I've had another lesson in the obvious: It's easy to raze and hard to preserve.

June recently emailed me a strangely dreamy black and white photo of the barn when it was newer, when it was crisp and white, and had two silos. In another email she wrote: "Our son wanted a board, any board from the barn. He wanted to make a memory." I directed her to our small mound of barn remnants.

Recently, I went back for a second visit to Leo's barn. He showed me the holes that still need to be patched, the places where he needs to add insulation, and the spot where he has to resize doors that are too big for the space. "The building is a total labor of love," he told me. "You don't know what you're doing it for. Inevitably it winds up being a storage room. And somehow you're never done." Leo, who did much of the work himself, estimates that he's spent $100,000 on the barn so far, and figures he'll need to sink another $50,000 before he's satisfied. I'm actually surprised that he spent so little, relatively speaking. Granted, our barn was in worse shape than his and we lack Leo's carpentry skills (I'm so-so with a drill, and Ed is more of a Super Glue kind of guy). But suddenly I get the feeling that we might have saved the barn for less than we'd believed. I wound up thinking something that occurred to me after other acts of demolition: jobs I've quit in disgust, romances I've terminated. Maybe we just didn't love the barn enough.

Read more from Karrie Jacobs on her website, and follow her @KarrieUrbanist on Twitter. And stay tuned for the next installment of Homeward Bound on Tuesday, July 14.

· All Homeward Bound entries [Curbed]