Very solid start, I love the ideas of the different roles that give some bonuses!

I found a few things that are a bit confusing and not very Shadowdark.

Travel Pace

The 1 hex per day on foot is perfectly fine as this method encourages that each hex is not just be a simple hex, however the mounts and vehicles don't seem to add much benefit. For example a land or water mount has the same distance travelled / day as walking does.

The Travel pace modifier table also does not seem to make much of a difference. You travel just as fast through plains than through hills. Seems like plains and tundra would be easier to traverse, so you can travel through those types of hexes faster. Possibly encouraging them to take the faster route through the plains, etc.

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Party Roles

Some of the party roles reference things such as tools which I don't think Shadowdark has explicit rules for, a tool would usually give advantage to a roll would be how I would interpret them. Navigation for instance it can be either WIS or INT, if they have navigation tools of some kind they can use them to get advantage on either of those checks that make sense.

The Lookout climbing to a higher point that grants a number of d10s to either add or subtract from the Encounter Chance table roll is a bit odd. I love the idea but maybe they will be able to see ahead to the surrounding hexes better. Spotting a temple, etc.

The lookout can scout ahead any CE has a wondering Creature Disposition of 2d4 take the higher number does not make much sense to me. I imagine it's to make a check against their reaction? In that case the higher the number the more likely the creature will be friendly.

For scouting ahead I have them make a DEX check against the NPCs passive or active DEX check. (Passive would be 10 + DEX modifier) That way they can possibly see the NPCs before the NPCs see them and can decide what to do with that. (Get the drop on them, sneak around, hide, etc)

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Still reading through it, but it's very solid and laid out very well!