That three hundred acre dairy farm WILL NOT generate enough income to support three families on it. The dairy business is going through a big consolidation right now. The starting point around here is 500 cows and then you go bigger. If you try it with fewer numbers then it just will not work. The net revenue is not going to be high enough. When the smaller guys are milking themselves they are just making the low wages the larger dairies are paying(illegal immigrants mostly)that is the competition.
Raising the steers out as beef will not really make you that much either as Holstein steers take much more feed to finish than a beef steer. Even beef breads would be hard to make it on in NY state. That state is a corn deficient area. They use more feed than they produce most years. So the local feed cost are higher. Then there is not any close beef processing plants. So your prices will be lower because of transportation cost.
If your wife is a manager of a bank then she will know about looking at cash flows from businesses. Farms today generate large gross revenues but not that high of net revenues. The livestock industry has had several bad years here with high feed cost. The dairy industry had several real bad years before that. Good friend spent 2008 and 2009 losing 100K a month. It took away most of his equity in his farming operation.
If the farm was profitable then the BIL would not have a problem financing the farm on his own. He has been in the business a long time and is having trouble making a profit. Your helping him buy the farm is just a short term band aid. He is having problems and is wanting outside money to help himself out. There are dairies quiting everyday because of the low profits.
With your education you need to look at switching careers away from teaching. It would be a much better investment to add to your current education so you have marketable skills in the private job market. Farming is not a high paying job. It sounds like you have been beat down and just are looking for an out. You could very easily end up financially bankrupting your family. Farming is not a very forgiving business to financial mistakes. So you would be out your money and not have good relations with your BIL. I would NOT recommend a family partnership.
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