I too have been looking for the perfect outliner for years. Grandview was definitely the best of the bunch, and still works in a cmd window (though not on 64bit Win7). After experimenting with many, I settled on Notemap from LexisNexis. It lacks the column features of Grandview (which I used for bug-tracking) but for text outlining is excellent, even if the output formatting is a little limited when transferring to Word etc. Doesn't appear to be being maintained/developed any more now, but is still available.
I keep experimenting with various todolist type programs (including Outlook Tasks) for bug and project activity tracking, but nothing is perfect - TodoList hereabouts comes closest, but it's activity timing is not really flexible enough - I need records of time spent each day readily available (that can be done) but I also need the timer to stop after a certain period of keyboard/mouse inactivity. Using the screen saver to stop the time is pointless when so many windows apps (Outlook for one) will stop the screensaver kicking in if they think you should pay attention to them...
One day, perhaps after I die, I will have enough spare time to roll my own. No, wait...