I don't outline anymore. Every year I've ever outlined, or done any plotting beyond basic idea percolation... I've failed. I just do best on the fly! Obviously, that doesn't work for everyone. Different methods and all that.
As for programs, I LOVE Liquid Story Binder
. It's got a bit of a steep learning curve, because it doesn't work like most programs, but it's SO powerful, it's got so many features, and you can run it off a flash drive. I got mine from giveawayoftheday a couple years ago.
It's a bit pricey, but they have a 30 day trial (and what do you know... Nano is 30 days) and usually he offers some kind of deal to NaNoWriMo participants.
If you want to try the writing environment, you can try momentum writer
. Free, very no-frills, saves in plain text format, uses full-screen mode (one of the best features about LSB is the ability to run it in full screen mode, so there aren't formatting bars or other distractions around.) and you can also disable your backspace key. Particularly useful for word wars, although I always have to turn mine on, because I type faster when I'm correcting than I do when I'm forced to keep going forward.
I have totally fallen in love with this program. The customer support is second to none, and I love all the extra features. Dossiers, image galleries, timelines, outlining tools, and more stuff I haven't even figured out how to use yet.
And no, I'm not an advertiser. LOL. I just really love this program. It's great for the free-for-all nature of nano.