The money I rolled over from the 1099-R to pay for a Life Insurance Retirement Plan(LIRP). Should I add the payment for the policy to Box 5 of the 1099-R?

You should enter your Form 1099-R as it is shown unless you have some reason to believe it is incorrect.

 

Click here for where to enter your Form 1099-R.

 

If your distribution was from a qualified retirement plan and it was directly rolled over to another qualified plan or IRA, within 60 days,  it would not be taxable.

 

 Click here for information on the taxability of your retirement withdrawal.