> My family farm is small enough they alone cannot support a entire family upper-middle class lifestyle, but the land is still worth millions.
This makes no financial sense to me. I call this: "asset rich, but cash poor". It is like living in a house that you inherited worth "millions", but working a job that "alone cannot support a entire family upper-middle class lifestyle". Simple solution: Sell the house. Cash out and invest in the stock market or rental real estate. You should do the same. If what you say is really true, then call Dave Ramsey (or someone similar) and ask for their advice. They will say the same.
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Small farmers are generally aware that this makes no financial sense. They're participating in a multigenerational family tradition. There are also typically relatives urging those still farming to sell the farm so they can get their share (which may not be that huge, when all is divvied up).