Tough call. I have a neighbor that has a good sized wooden barn that I figure is 100'x60' and his was in at least as bad shape as yours when he bought the place. My thought was to knock it down, reuse the good wood, burn everything else. Good thing he didn't read my mind. He shored up the drooping walls and door ways, replaced the bad wood, really fixed it up nice, outside and inside. AND he painted it barn red, trimmed in barn white. The upper hayloft is now a completed office area for his business, and the lower area is now his shop. I wish that I had pictures of it when he took it over, and pictures of it now. I'm telling you, if that had been my barn, it would have come down before it killed someone, was my thought. I was way wrong.
A farm that I considered buying before I was outspent by the Amish Bank, and they were outspent by a doctor whose wife wanted to raise horses on, had several barns, one for cattle. Huge barn that was breaking down, starting to sag. The folks that owned it brought in a portable saw mill with a 48" blade, cut new supporting beams, 18"x18" from oaks on their property, jacked and shored it up, moved the new beams through the lower cinder block walls, fixed the barn up. I looked it over, that was a job. When I was outspent, they still kept cattle below, kept tractors up above, and had a used hay loft above. Strong barn.
If I were you, before making such a decision, I'd figure out what my needs are and price a new barn, inspect the construction of what you have and the cost of repairing it. It's your money, your life, your decision to live with.
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