When do you build roads

I will generally build several cities very early on, so roads are essential not only to increase commerce going forward, although often the early cost has to just live with itself, but also to increase unit movements.

The cost of roads is largely a secondary concern, the primary to me being where my units are going to be built, what sort of city specialisation I'm going to have and the availability of strategic and luxury resources.

If I've got a city that has only duplicate resources, then it gets a road almost immediate because that's good tradin'!
 
I always build roads, as soon as I have The Wheel, at least two cities, and an available worker. I've never actually paused to do the math, but it always seems that the trade route :c5gold: is more than the road maintenance cost.
 
When workers are available... I try to go lean on stuff, even workers, as workers have maintenance as well. That means the workers I have are most of the time working on tile improvements that give a big boost to gold. For me this happens when I have 3 to 4 cities. It's when I'm somewhat hesitant on expanding more as connecting resources may delay my attack, and the payoff from lux may be very minimal due to souring diplo relations.
 
another reason not to build early roads is if you go for super-early RAs. Delaying the research of the wheel seems to be a key part of maximizing early RA value.
 
I build roads once my workers have started to run out of resourced tiles to improve. A little sooner if I have a lot of hills/forests/jungles bogging my movements down.
 
If I've got a city that has only duplicate resources, then it gets a road almost immediate because that's good tradin'!

Roads are no longer required to hook up resources for use/trade.

I'm about on par with everyone else around here. My rules for building roads once one of these four conditions are met:
  • Afraid an aggressive neighbor will declare on me soon or I want to declare on someone else and most of the terrain is rough.
  • Lots of hills/jungles/forests around rivers are also a consideration if I already have the tech (engineering I think) that allows roads to help across rivers. This is to help my workers get around faster.
  • No other pressing tile improvements to build and my cities are above break even (general rule of thumb is 1 citizen per road required to connect the city)
  • I have Meritocracy and need the happiness to stay at 0 or above.
 
I build them right away. Usually by the time I get the wheel, my cities have grown reasonably well.

Even if I lose money at first, they are important for defense.
 
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