Yea, strategy and finesse don't quite work when you have hordes spawning and moving to every single border region you have at the same time, and then appearing in another once you leave. Besides, some regions we have held for weeks and raised production to their highest, yet we are still stuck with cruddy roads.
Roads take a while to repair, the more war torn the land... The more terrible the road becomes. Think of it as a chaotic road with a bunch of bandits and wagons idley flipped... Plenty of holes too.. trees blocking ways.
The moving through of destroyed roads is also part of strategy. Certain roads that lead to your target region may take 5 turns to reach. However... Another region bording it may only require 2.
Those poor... Poor... Roads.