Not sure how feasible or actually useful it would be, but what about a History tab in the Board Designer that simply logs out actions taken on a map.  Nothing fancy really needed like undo (unless you really wanted to), but just simply a log.  Seems like it could help with some confusion.  Mainly useful for territories/continents/borders but could add all board changes in and a few colors to make it easy to view.

Example:

1. Uploaded map image.
2. Added territory YA.
3. Added territory YB.
4. Added territory YC.
5. Added territory YD.
6. Added 2-way Default border YA to YB.
7. Added 1-way Default border YA to YC.
8. Added 1-way Artillery border YA to YD.
9. Added 1-way Fortify border YD to YA.
10. Added continent ContY (Territories YA, YB, YC).
11. Removed territory YA.
12. Updated Rules.
13. Updated Player Colors.
14. Updated Cards.

Maybe it's not easy or useful, so just a thought.

*edit* Forum bug, number list above 10 looks bad :P

nice. didn't see this somehow.