Hay baling equipment "is one of the most dangerous types of farming equipment."
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National Ag Safety Database - National Ag Safety Database
Also quite expensive. You might want to run the numbers on that. You can usually work out an arrangement for someone to bale your hay and they keep part of it. Which makes more sense financially?
You're going to get very different advice from people who are experienced with heavy tractors on mostly flat land vs folks newer to the rural life, and especially those with hilly property. I think a lot of flatlanders have no idea what it's like in our kind of terrain. For example, if your WV land is hilly, an older Farmall may be risky:
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If you're not mechanical, you'll need to learn all that unless you have shop nearby, especially with used equipment. Again, some of these folks with decades of experience wrenching on machines don't seem to understand how clueless we nonmechanical types are about this stuff.
Worries me a little to hear of a newbie wanting to take up haying, especially on hilly property, and especially with older equipment, which often lacks safety features. Have you ever been around haying equipment when it was running? I have (a lifetime of horse obsession and hanging around farms and barns) and I truly admire folks who can run this equipment. It is very intimidating.
Of course if your life's dream is to take up haying, do your research and go for it.