If its now "free and clear", you might want to consider selling to him on an owner contract (may be called "contract for deed" in your neck of the woods)- You would be the "banker", so his credit doesn't matter. I'm thinking you probably want to do it this year if you're going to, as I believe the favorable tax treatment on capital gains will go away in the future.
But if he's happy renting, the land will probably continue to increase in value (unless everything crashes), so you may want to keep it as an investment or to give to your kids.
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Today's Featured Article - Memories of a Farmall C - by Monty Bradley. When I was a child, my grandparents lived on a farm owned by a Mr. Walters. The crops raised were cotton and soybeans, with about forty head of mixed breed cattle. Mr. Walters owned two tractors then. A Farmall 300 on gasoline and a Farmall C, that had once belonged to his father-in-law, and had been converted from gasoline to LP Gas. Many times, as a small boy, I would cross the fence behind the house my grandparents lived in and walk down the turn row to where granddaddy would be cultivati
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