I think that roads should be a production job, and at the start of the game, they will only go to other cities that are fairly close by. Trading would double the distance a city looks for another city to connect to with roads, and add a production job for 'Roads to nearby outposts' while Economic would add jobs for 'Connect roads between outposts' and 'Build roads to faraway cities.'
If an outpost or city is destroyed then any roads that connect to it should fall into disrepair.