Any time you start a tenant on insurance you will be required to immediately take a payment. Select the tenant and then go to Tools -> Start/Cancel Insurance
A message will appear letting you know the tenant does not currently have insurance so you must select the level of insurance they want to sign up for:
The coverage options will be displayed based on the settings configured when you set up the insurance module. Select the appropriate coverage level and click Start Insurance
The system now notifies you that in order to start insurance you MUST be prepared to take a payment. There is NO way to charge the tenant later. 
Click YES and continue with the payment. This tenant has now successfully been setup with insurance. The insurance fee will automatically be included in their total amount due per month. In the tenant information window you will notice the Amt Due Mo is greater than the rent.
If you click on the Amt Due Mo button you will see the breakdown includes $30.00 in rent and $6.00 in insurance.
