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I have heard of other sole props who take the deduction year after year and haven't had any problems. I really think your position is defensible, and the IRS agents I spoke with didn't come out and say "don't do it". In fact, the agents seemed to skirt the real question, even after I explained my exact circumstances.

The intent of the law was to give self-employeed people a deduction, and I think the waffle words in pub 535 was to give people leeway. If you are solo business owner (no employees), then it make sense to me to take the deduction.

If you have any suggestions on formalizing an insurance "plan" for sole props, I would like to hear it.

Health insurance is VERY expensive. I was tempted to flame the IRS agent when she suggested I get insurance under the name of of the business. Group policies, at least where I live, are 2 times more expensive than individual policies. It is not like I have a cool $1,000 or more to drop on health insurance every month.

One other thing I'm in the process of setting up is a Health Savings Account (HSA), previously MSA. Contributions are deductible and disbursements for medical expenses are not taxed.

Thanks for listening, and sorry for all my ranting!
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