Hmm, how would you "notice that the innkeeper is waiting for the wood"? Many people in skyrim are standing around anyway, hah.
The bandit event could be scripted,and the horse one could possibly be scripted too.
Given that NPCs now already have some form of "routine" everyday, i don't see why faendal couldnt be scripted to deliver wood to whiterun at certain intervals and such. And uh, Jarl balgruuf could be scripted to take a walk every week or so? Its quite possible in my opinion.
The thing is an npc doing the exact same thing in the same intervals isn't dynamic. Dynamic implies change.
And that type of approach has been done, in Oblivion.
That one Countess would visit her mother every week, some of the alchemists went out, & gathered ingredients every few mornings before opening shop, the elf in the DB made her rounds of the various cities every few days. But that isn't dynamic, none of that changed in response to stimuli, they kept doing it every week no matter what.
A dynamic world would be a world like that at first, but one that would evolve slowly with every action, & reaction. And that's a lot harder to do.
I really shouldn't have laughed at this as much as I did.
I'm just being honest. When your playstyle tends towards combat inept builds like "trader, cartographer, or doctor" you tend to need a lot of saving.