Stick a fork in it. It's done. We have high input prices and low crop prices the next 18 months, maybe longer, if he is in that deep he won't get out.
What to do from here? If you stick more money in propping him up, you stand to lose whatever you put in.
If you can offer some opportunity for him at low risk to you, great.
If you walk away, could be hard on the friendship.
If you follow up with collection proceedings doesn't sound like there is much to collect on, likely really hard on the friendship.
Pick your poison.
Me, I would try to be supportive but walk away from dealings with him, farming is hard enough to get sucked down by others at this time. Sounds like not much to collect so unless he files bankruptcy himself, I guess chalk it up to experience and move on myself.
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