I'm taking the plunge off the Outlook cliff and trying out a standalone task management program featured on LifeHacker. It's called TaskCoach and it's a free, open source program available for download from SourceForge.
So far I'm liking it. It's relatively straightforward, but, unlike Outlook, let's you easily create sub-tasks. It also offers an uncluttered view of your daily tasks with easily configured views via a "Filter Side Bar." This ease-of-view is a revelation compared to Outlook. Basically it's a one-click process to see tasks by category or status. Brilliant!
TaskCoach handily minimizes to the taskbar when closed or minimized for easy access as you work. In addition it has built-in effort timers (which I hope I never feel compelled to use, but it would probably be for the best).
The author actively solicits ideas for improvements, which gives me hope that one day it will become even better. I already have a few suggestions to make including templates, drag and drop functions, and the ability to set a default attachment folder.
Anyway, I'm going to try it out for a week and see if I can handle losing the biggest plus of using Outlook for task management, which is the fact that I can drag and drop an e-mail to create a new task, complete with the body of the e-mail. A handy VB script I found even lets me include attachments. This really has been my only reason for sticking with Outlook. However, I can already tell that if TaskCoach offered the ability to drag and drop e-mails to create tasks I'd be sold already.