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JohnH, you are correct on being subject to the penalty. I see three 1099MISC forms but from his expenses he may have missed a couple. This guy is a mess. You would think the penalties would get his attention. Personally, I doubt it. I have been charging him a substantial rush/last minute too lazy to get docs in a timely manner PITA fee each year. He only complained once and threatened me with going to another preparer. Needless to say, I invited him to go. Well obviously, he didn't he's still here and still getting charged for causing me to sit in front of my computer to beat the 12:00 midnight time. I'm going to nail him this year as he is screwing up Monday night football. I would normally say too bad so sad, but if is willing to pay the fees then I'm willing to collect them. I think Forrest Gump said it best. "Stupid is as Stupid does"

If a Sch F is similar to a Sch C, and if my memory is not too fried tonight, a self-employed person can provide health insurance to his employee/spouse for the employee's whole family. It's deductible to the SE taxpayer, I think on Sch F, because it's for the employee. The SE taxpayer's own Medicare premiums are deductible as SE health insurance on Sch 1 line 17, income allowing, with any excess to Sch A line 1. But, don't trust me on the above! Two more complex returns to get done, and not much sleep last night, or for the last week or more or...! So, research more yourself or wait for someone to jump in with cites for you to rely on.