First the backstory:
I got out of grad school in 1997 and started working and trying to use a DayTimer. It did not work because it was huge and ugly and I hated carrying it around. In February 1998, I bought a Palm III, which worked well for me. It was fun to use, and always with me. I have used PDAs ever since.
The things that made the PDA work for me were that it was always with me and that it forced structure on me. I could not cram paper into it or write in the margins. I had to do it right. However, this created a messed-up thought process in me: it made me think everything has to be all digital or all analog. There can be no intermingling of the two. I have no idea where this came from, but it became my predeominant way of thinking. It was like I was afraid of betraying the PDA cause, having too much to carry, or something else crazy.
Fast-forward to today:
I have a Treo so I don't have to carry planner and (e)books and phone and to-do list and notepad and address book, etc. However, now I have read GTD and now cannot live without the GTD Outlook Plug-in.
Yet there is something unexplainably intriguing about the Hipster PDA and the Moleskine. I cannot give up a digital planner (my addresses just HAVE to be perfectly alphabetized). Even though I am, after eight years of PDA use, pretty darn fast at input, I have found I am less likely to write down everything in the Treo as I am in my (just made today) hPDA. I also spend WAY TOO MUCH time looking at Treo-related junk online when I should be actually living life.
The Hipskine (desktop + moleskine) is an idea I never thought about. It seems redundant, but GTD is not about the fastest way. It is about the best way, right?
If anyone is using some combination of PDA/Smartphone and paper, I would love to hear how you make it work.