As far as the overworld travel goes, I think there are a couple areas that might clear this up if they were changed or specified more clearly. Note that I have tried not to read much in terms of instructions (aside from patch notes and the initial tutorial). Also, if this ends up rambling on too much or becomes pointless please feel free to ignore it
It seems to me like there are 3 major areas of exploration - roaming the world map, sending settlement members out to scout, and actually going into the different squares (shows up as green on the overworld map).
When I started, I was running through the different squares and visiting everything. Later, I started going into each square so that they were all "100% scouted" as far as the surface level went. Then I realized I could send my people out to scout, so I have done that as well. I've just realized how to actually explore and find good stuff, so now I'm in that phase (mostly underground, going to find towers, etc.)
I think it leads me to 4 fundamental questions about the game:
1. What is the purpose of visiting or exploring surface areas?
2. What is the purpose of roaming the map?
3. What is the purpose of sending scouting parties?
4. How do I decide where to spend my time?
The answers as they seem to me now:
1. To get to specific things (commodity towers, etc.)
2. To travel to the good places (commodity towers, etc.)
3. To expand the overworld map, find new settlements and wind towers, minibosses etc.
4. Ignore the majority of the world and focus on the places that I know will have good stuff.
Rather than feeling too easy, the overworld travel map almost feels pointless to me at this time. I think that if the overworld travel, scouting parties, and physical exploration or areas were somehow tied together in a more cohesive fashion it could add another dimension to the strategic game. As it is it feels like there's a huge world out there, the majority of which is kind of pointless.
Of course, by the time I finish writing this post everything could have been overhauled again, which is kind of why I love playing in these betas. I haven't really opened AI war since the crazy daily patching stopped