These days, when I get the frequent “How’s the house going?” question, my answer is that our remaining big-ticket items are the rain gutters, siding, and carriage house. I have a contractor hired for the gutters, the siding is on tap for summer 2013, but the carriage house is a story unto itself that I only tell if they really want details.

If I recite the carriage house’s litany of problems and recommended repairs (a long list of structural reinforcements), the inevitable next question is, “Have you thought about just tearing it down?”

The answer, of course, is “Every day”. The dilapidated carriage house roof is the first thing I see every morning out the bathroom window. I see its paintless siding every time I let the dogs out. I see its waterlogged door and missing windows every time I look out the kitchen window. I see that horrible mess of a garage door in the alley every time I arrive home via Calumet.

But, I won’t.

The first that stops me is history. I didn’t buy a historic home to bulldoze the inconvenient bits. Once you tear it down, even if you rebuilt a perfect replica, it’s now your replica of an 1899 carriage house, not your original 1899 carriage house. Shortcuts would get taken. I’d be persuaded to leave out features from the original that tack on excessive costs. It would inevitably be diminished.

The second thing that stops me is logistics. You can say it would be cheaper to bulldoze it and rebuild, sure. But have you really thought that through? Where are we storing everything inside it in the meantime, and who’s moving it there? Where will the dogs run while our backyard is a construction site? Who’s going to hire the architect or engineer, building contractor, and demolition folks? Who’s going to get all the permits and approvals required to raze and rebuild a structure that lies flush with the public alley and my neighbor’s yard? Is it even still legal to build such a structure where it is? How many modern extras will get tacked onto the price tag because it’s “far cheaper to do it now” during the rebuild?

And finally, where the hell do I get the money for this all-at-once approach? I’m not sold that it’d even be cheaper, and at least I can do repairs in phases stretched over years.

Money isn’t the only factor when planning a project of this size. I’m dubious of my ability to finance full repairs, but I’m downright incredulous of my ability to plan and build a worthy replacement.

So, yes, I have thought of it. And I think it’s even crazier than my desire to save one of the last carriage houses in Woodbridge.