When do you build roads to city states?

There are no special bonuses. Only emissaries faster on the way there will come running. Or religion press will be bigger.
 
It can connect your cities if they are blocked by a city-state's territory(if you allied or are friends with them of course).
 
When? When city state is large enough to pay itself for the most part of roads. Not before villages can be built. As I deploy the road, I'm certainly going to trade with the city state, so I put some villages on the road.
Note that villages between one of your cities and a city state only gives the bonus for the trade route, not the city connection (unless you're connecting to one of your cities on the other side of the city state).
 
I got a CS quest to connect with a road recently and I've never seen it before. Is this new for the 2/27 version? Are there special conditions to trigger that quest?
 
I got a CS quest to connect with a road recently and I've never seen it before. Is this new for the 2/27 version? Are there special conditions to trigger that quest?
Before 2/27, the quest was bugged to not appear. Gazebo fixed it.

I connect to friendly/allied city states if they are part of the border between me and rival civilizations. City states are generally too weak to stand up against another civ, so they need to be protected if you don't want them crushed by your opponent.
 
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