With your approach, I see the effect you’re describing, but I don’t yet have a clear picture of the process that produces it. If you’ve already laid that out and I missed it, my apologies. But if you walk me through what it is you do, I think we could pinpoint where our methods differ and what the consequences of those differences are, like I did with Torchbearer.
So, running Stonetop is probably not the best example because it has >280 pages of incredible setting details and tons of tables and bits. It
does encourage the sort of constant player-directed questions I've posted numerous times here - but it's got a pretty decent regional map, so if you're in "The Flats" you have suggested Discoveries or Dangers; and tables to roll on.
I guess here's an example somewhat similar to the last play extract you posted:
Situation, two of the characters are returning from Marshedge, the only town of serious significance in The World's End (the region of play). They've gone there with a caravan of folks from their town to do some trading, some recruiting, and follow-up on some bird-messages one of the other characters has been sending.
It's a 10 day trip via the Maker's Roads to and from Marshedge back to Stonetop (the village where all the characters live and what the premise centers around). On the way back, we examined some of the stuff between the Marshal and his sister (NPC), regarding his dead brother and the legacy thereof (color, but important color around relationships - the player had even pre-written an entire dialogue he wanted to get out).
And then when we cut back to the caravan after seeing what the two characters back in Stonetop were up to, we time skipped forward a bit. I looked at my Agenda (previously mentioned, includes "Punctuate the PC's lives with adventure"), the entry for the area they were passing through (the Steplands), described a bit of the hills around them and asked a couple questions, scanned the entries for the Dangers of the area, and realized that one of them is a massive bear-sloth thing that is noted "you'll round a bend...and there one'll be...taking a nap." They're on a big magic stone road in the summer, and I figured that fits well!
So I
Reveal an Unwelcome Truth, one of my GM moves, at the Ranger who is routinely scouting a little ahead of the band and tell him that he sees this house-sized lump of fur curled up in the middle of the road right where they need to go, and
"what do you do?"
Things went along, and turned into nearly having to try and fight this massive creature off (it wanted to eat stuff out of their wagon, or really the well seasoned wood of the wagon itself) despite the magic of the roads; but through some use of scouting and ideas they managed to negotiate with it instead and direct it off to its favorite trees over a hill.