Hi, Tmoehring,
Congratulations on your retirement!! Yes, you will get a 1099-R for your retirement plan distribution. Usually that money is federally taxable (state tax rules get a little more complicated). If you haven't already, you may wish to consider having tax withholding done by the payor.
As to your health insurance premiums, deducting them can be one of the big perks of self-employment. This article will tell you more. If you are not self-employed, you can deduct them as an itemized deduction if you meet the requirements and they exceed 7.5% of your adjusted gross income. Here is more detail. However, that deduction will only benefit you if you have enough itemized deductions to exceed the standard deduction. These days, most people take the standard deduction.
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