Yes. The IRS has indicated (https://www.irs.gov/pub/irs-wd/1228037.pdf) that all Medicare premiums are similar to other health insurance, and that this deduction rule extends to Medicare premiums for coverage of a self-employed individual’s spouse, dependent, or child under age 27.
Rules limiting loss deductions to cash investments and personal liability notes. An exception for real estate treats certain nonrecourse commercial loans as amounts “at risk.”