To House, or Not To House

… and that is the question. What is the more-likely thing that a person might say: “I took on a historic house that needed a lot of work as a new chapter in my life, and it’s the most satisfying thing I’ve ever done,” or: “I bought a historic house that needs a lot of work and it was the worst decision I’ve ever made.” Should my next chapter in life come with a challenge? Or should I take an easier road and find peace and relaxation?

Let me back up a minute, and explain where I’m coming from with all this. My girlfriend and I saw an intriguing Mission Revival home on Zillow, but that’s not even an accurate first description – it’s really an “estate,” with a historic house, an old barn, a second house, and several sheds on 2 acres. I don’t want to get into specific addresses or locations quite yet, because I just saw it a little over a week ago, and it’s still on the market, and I’m still thinking about it. A lot.

This is the quandry – this property needs a LOT of work. It’ll probably cost a lot of money and I’ll have home improvement projects for the next ten years of my life. Do I really want this? The logical answer is no – it sounds like trouble. Do I really want to wake up every day with another home improvement project to do? But there’s something about it: there’s a historical aspect to the house (it’s on a registry of historic places and even has its own Wikipedia page). There’s the charming details of an old farm house which was turned into a “country estate” by a successful NYC businessman in the early 20th Century. There’s the income potential of a second house, and a glorious barn (which is old, beat-up, and maybe ready to fall over) that could be used in a variety of ways. This barn could be an art gallery exhibition space, and I could integrate some antiques and home furnishings, or – if I didn’t want to pursue a commercial endeavor, it would make a fantastic studio to make big paintings and sculpture. The barn could be a performance space, an event space for rental, it could be all sorts of cool things.

I mean, this could be a once-in-a-lifetime opportunity, right? Or this could be a bad decision caused by Zillow-induced intoxication leading to financial ruin and a sore back.

antique phone in country kitchen in upstate NY
An antique phone in a country kitchen in upstate NY – is it a stylistic prop, or has it been there 100 years?

A couple other things to consider – it’s upstate New York, in an agricultural district with farmland, but also close proximity (approximately 15 minute drives) to 4 or 5 different hip upstate towns, filled with restaurants, antique stores, art galleries, boutiques, and other interesting places filled with people who might be very interested in a new arts and antiques venue in the area. But it would be a drastic change in lifestyle – I grew up in a large city in the midwest, lived in NYC, and had a comfortable suburban lifestyle for the past 25 years. Do I see myself ready to get on a tractor mower to cut 2 acres of grass? Do I see myself fixing a barn?

Granted, I could hire people to do those things, but part of the challenge, part of the allure, is the question of whether I can do any of this myself? It’s a question of whether – after 20+ years of working a desk job, can I use my hands to build and fix things? Am I kidding myself? Or can I YouTube video tutorial myself into a rural handyman?

Just for fun, here’s a glimpse of my vision … first we have the barn as-is right now … followed by the same wall of the barn as a finished art space. What do you think? Can I create an arts destination next to a field of wheat?

inside of a barn in need of repair
The inside of a barn in need of repair.
barn transformed into an art gallery
A conceptual image of how I could turn the barn into an art gallery.

I should add as a final note here, my consideration of this property is not all about creating a new arts and antiques space – I would see that as a bonus, not the sole focus. My attraction to this property is primarily the charm and excitement over a grand, historic house, plenty of open space, a new lifestyle, and the potential of multiple structures … and did I mention that there’s also a pool?