In order to achieve the list behavior I wanted, I had to create a custom workflow.  The problem was I wanted to have a task list feed into a calendar.  I wanted this because I still wanted to keep the Outlook connectivity.  By using Sharepoint Designer, I was able to create a simple workflow.  I added a two new fields on the task list.  One was a Yes/No field that acts as a trigger.  Once this value is set I'm then adding a new item into the calendar.  I use a variable to combined the Title and the other custom field into Event Title on the Calendar.  It works great!