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Lamaze childbirth classes are deductible as a medical itemized deduction subject to the 10% / 7.5% AGI limitation on IRS Schedule A. However, classes on caring for newborns or on fetal development are not deductible.

Massage therapy sessions for general stress reduction, even if recommended by a doctor, do not qualfy as a medical itemized deduction.

The amounts withheld from your paycheck for medical insurance is added to other medical expenses, such as for doctors, dentists, and prescription drugs.
The total medical expenses are subject to the 10% / 7.5% of your Adjusted Gross Income limitation and the excess is deductible on IRS Schedule A as a medical itemized deduction.

The costs of travel to and from your doctor's office are part of your medical itemized deductions on IRS Schedule A subject to the 10% / 7.5% of your AGI limitation.
You may claim the actual travel expenses, or the IRS allows a 24 cents a mile flat rate, plus parking fees and tolls.

Certain limitations apply. The costs for lodging while receiving treatment at a licensed hospital or outpatient clinic is limited to $50 per night per person.
If both parents travel with the child then $100 is allowed as the maximum lodging deduction per day.
This amount would be added to the other medical expenses subject to your 10% / 7.5% AGI limitation on IRS Schedule A for itemized deductions.

Payments to psychiatrists, psychologists, medical doctors, dentists, eye doctors, chiropractors, physical or occupational therapists, acupuncturists and medical care psychoanalysts, plus other medical payments, are itemized deductions subject to your 10% / 7.5% AGI limitation on IRS Schedule A.

Unreimbursed payments for long term care services for chronically ill individuals are deductible medical expenses subject to certain age limitations and to the 10% / 7.5% AGI limitation on IRS Schedule A.
For year 2016 the maximum deductible premium amounts are $390 if you are age 40 or younger , $730 for those ages 41 - 50, $1,460 for those 51-60, $3,900 for those age 61-70 and $4,870 for those over age 70.

Qualified long term care insurance contracts will generally be treated as health insurance for purposes of the self-employed health insurance deduction on IRS Form 1040 page 1.

You only have to attach Form 1099 if there is any withholding listed on the 1099 form.
Do not attach your copies of Form 1099 to your tax return if no withholding is listed on them.
Keep them with your copy of your tax return.

Tax-exempt interest from municipal bonds, exempt interest dividends from a mutual fund or other regulated investment company, although not taxable, is reportable to the IRS on Form 1040 line 8b, as well as on Schedule B.

Enter the total interest income amount on IRS Schedule B line 1, and under the subtotal of all the interest income, enter the 50% amount owned by your brother as a negative amount with the description "Nominee Distribution".