[Polydamas]

Some of the reasons why good roads were uncommon historically also work in the Wasteland:

- Roads let merchants and goods through, but also invading armies. So being at the end of a snaky mountain road has its advantages (Afghanistan still has almost no railway network because of considerations like this)
- Everyone is tempted to try to collect taxes and tolls, while pressure to spend them on the roads does not always exist
- The benefit of roads is unevenly distributed: most of it goes to the destination, and to travellers, but most of the length of the road goes through thinly populated rural areas with no money and nothing much to sell. So if the polities are small, some may just not want to bother to keep up the roads.
- Everyone along the path of the road has to agree on some things like the direction of long roads, rut/lane widths, capacity of ferries ... but being stubborn on one of those things is a good way to show independence, or people get worried that accepting someone else's weights and measures leads to slavery.
- Resources are scarce, and there are lots of other ways to use the resources which would be used building and maintaining roads

So there should be places where someone deliberately broke a road or tore town a bridge to protect their town, places where a militia is charging ridiculous tolls, places where the locals refuse to do maintenance and avoid travellers, places where some local potentate made them tear up the roads and rebuild them to a new standard, and places where they are salvaging the roads or just ignoring them while they work on another urgent project like keeping the dam from bursting or building the Anti-Mutant-Wall-Which-Shall-Never-Be-Crossed-Praise-Thelohd.

Edit: The resulting Area Knowledge and Current Affairs rolls to pick routes with good roads and few tolls or bandits, and social skills to get local help crossing rivers or bridging gaps or removing deadfall, also give someone other than the driver and the tech a chance to shine in a cross-country adventure.