Overall I don't think this is useful. They might or might not get good results. However it is really hard to beat the farmer/laborer who lives close to the farm and thus sees things happen and can react quickly. There is also great value in knowing your land, though they should get records of what has happened in the past (this is all in a computer, but you won't always get access to it when you buy/lease land). Farmers are already using computers to guide decisions.
My prediction: they lose money. Not because the AI does stupid things (though that might happen), but because last year harvests were really good and so supply and demand means many farms will lose money no matter what you do. But if the weather is just right he could make a lot of money when other farmers have a really bad harvest (that is he has a large harvest but everyone else has a terrible harvest).
Iowa has strong farm ownership laws. There is real risk he will get shutdown somehow because what he is doing is somehow illegal. I'm not sure what the laws are, check with a real lawyer. (This is why Bill Gates doesn't own Iowa farm land - he legally can't do what he wants with Iowa farm land)