For additional nerdiness, my PC will always have to carry a quill, ink, and parchment, in order for me to update the journal
Great idea, I'll do the same.
About first point - I probably won't do it, because I have too many other activites such as regular job

girlfriend

, sport, ... and if I focus my whole free time solely on Skyrim + keeping real journal, that wouldn't be alright.
Otherwise, I never fast travel, perhaps with carriages only but we'll see about that.
I drink and eat at least two times per day and sleep at least six hours, usually nights, but I might also take daily nap.I almost always walk, except if it'll be real slow, then I won't and will wait for some speed mods..
I probably won't go with
dead is dead, because I'll definitely get too fond of my first character.
Besides, I'll probably play the game really really slowly, enjoying environemnt, doing odds and ends, taking walks and thinking where to find Dark Brotherhood - my first character will be evil, not ultimately evil, but still.This will be my 1st time that I'll do my 1st playthrough with evil guy, I usually play good guys.