Worst install of the year: TurboTax2004
So I remembered why I didn't manage to get my taxes done this year on time. It was because TurboTax 2004 refused to print them for me. The problem it had was that it wanted to update one of the files for the tax returns since it didn't have the right information on time for it's Dec. 2004 shipment date. This should have been fine since they invented a system called "One click update". This one-click update mechanism pops-up when you reach the last step of your return and you go to print it or when you first load the software. So I hit that one-click update button and the system went into what Turbo Tax support refers to as the "TurboTax 2004 update loop". In their own words....

This issue presents itself as a seemingly endless "loop" and occurs after you've downloaded a TurboTax update. It begins with the following message, which appears after starting TurboTax:

Updates not installed. There is an update for your TurboTax. Would you like to install the updates now?

Basically this leads to constantly being asked to reboot your computer with the only solution to forcibly remove this program and anything that ever touched it from your computer. I have now done so and will attempt to reinstall it (plus the Free state add-on) having to enter the memorable code 9481C5EA93F62103 and the last eight digits of the credit card I paid for this software in order to activate the installer.

It is ironic that the company that makes this very frustrating user experience is called Intuit, as in Intuitive, since this process is far from intuitive.
Wish me luck...