I am very sympathetic to your concept of being paperless. I've been trying it myself for a while. I also like the idea of using Apple gadgets to do so, they are already my pets. I still agree with Malcolm Gladwell that only digital media isn´t enough. First I like the physical act of writing and, my practice showed me, nothing is more simple and straigthfoward than take quick notes on paper. So, my plan is to use paper for thought, digital media for storage, organization and fun.
What is working for me right now is:
1.Loose leaf (breast pocket)
Bucket (in GTD sense) for quick notes, daily checklists and ideas.
2. Notebook (moleskine-like)
GTD lists and contexts, reading summaries, plans, follow ups.
Calendar, contacts, passwords, chess, music, movies and podcasts.
Readers: Kindle, Bookman
Quick notes: Scribble Lite, Fountain Pen
Chess: Fritz, Stockfish, Schroedder, GameClock
Assorted: aSleep, iLuvMozart, ArtLite,Moleskine,Convert Units,Y!Music,Twitter
4. Other resources I found in my way:
Journaling Arts Blog and Store
Post-it and the book
Visual Notetaking and Visual Problem Solving
Making your mind your playground
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