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!
I ran into some issues with the web application stress tool on Vista x64. I need to download the dll msvcp50.dll from the DLLfiles on web. Then I copied it to the following locations.
Then I ran the setup.exe and it installed successfully.