It is picturesque--congratulations! And I can appreciate the historical use and value.

But...if you are thinking about throwing money at it, and living in it...what sort of overall condition is it in? How is the roof structure; the wall structure...does it have working HVAC, electrical and plumbing?

Do you think it would be cheaper to sell the barn and have someone move it; or demolish it...and build new?

I see no pictures and I am a lover of renovating old houses but you need to check out the prices in your area.

Yes, you'll need to check with contractors in your area.

I'm in western Canada, and we have a friend who converted an old one-room schoolhouse into a summer cottage on some land a family member owns and farms. My husband, who's a builder, did the work, but it's not winterized or suitable for full-time, year-round living. It has running water and a woodstove to take the chill off the spring and autumn mornings and evenings, but that's it. Our friend spends most of October to early May in the city, and then spends the rest of the time at the schoolhouse cottage in the country. You may want to consider something like that for the building, an extra space for the summer months, for entertaining or as a studio or quiet getaway from the main house.

Looks like fun but a labor of love. Would love to follow the progress.

This thread might be helpful when it comes to deciding what to do,

https://www.gardenweb.com/discussions/4453577/farmhouse-renovation?n=244

What can you keep? The framing. Everything else has to go, foundation, siding, roof, etc.

It could turn into a wonderful renovation in the end, but -- yes -- it'll be an expensive and difficult journey.