I can't offer much in the way of suggestions for syncing org-mode with meat-space (notebooks).  I do know something about field notebooks, however.  I am used to carrying around a notebook in a waist pouch (some of the locals call them "thunder bags"), and have been doing so for years.  The best notebooks I have found for general use are those I have cut from marble covered composition books.  At the printer's I pay a couple of dollars to have a stack of three or four notebooks cut into convenient sizes.  These books are about 19 x 25 CM.  Whatever works.  I have them cut into sizes convenient for whichever brand of pouch I am carrying, usually about 7.5 x 4.5 inches (11 x 19 cm, or so), sometimes smaller.  As a side benefit, leftovers forml smaller notebooks of various sizes.   They are sewn, so no metal to rust, and the thick cardboard covers are ideal.  They hold up much better than the little mini-marble notebooks.   Printers use Guillotine knives, and can easily trim a stack of notebooks to any desired size.  Cheap and available almost anywhere (?).

After a typhoon destroyed my home some years ago, the only notebooks that were salvable were these comp books.  Pencil notes are generally readable, but  not always.  Some people use ball point pens in the tropics.  Duing three years of undergraduate work, when I was taking notes constantly, I experimented with many types of fountain pens, for water proof, india and drawing inks.  I found a Mont Blanc fountain pen in about 1985 that was fairly cheap at the time (not anymore, I'm afraid) that held up better than any other, and never clogged, even with India Ink.  Eventually I even used these pens as a laboratory pen, for writing labels and lab notes.   I don't know whether Mont Blanc manufactures them anymore, but the pens I have seen in duty free shops are far too expensive for me. 

In my case, field notes were eventually typed into a sort of free-form database in what linguists refer to as "band format."   I now have a remember template for transcribing notes into this format.

More than anyone wanted or needed to know, for what it's worth.

 

Alan Davis