Telegraph Road - Natural Growth

Huge expansion at the other side of the tracks! In no time the town has grown an extra 50% (give or take)! Probably at some point you'll need a second crossing point between both sides of the city, as that at-level crossing will easily become a chokepoint once the rail traffic increases.

I also found playing natural growth particularly challenginng in C:S. When the game was released, Dirk gave me and other players early access to the game (were you one of those too?) and I CJd for a week or so, showing the novelties of the game. Wanted to take it easy, in a similar approach to yours, but the village grew almost incontrollably out of my hands...

I like how the separate grid based sections follow the contours of the primary established roads. This is a realistic organization of street networks. While @TekindusT mentions an important point about creating additional crossroads connecting the parts of town opposite the railroad tracks, I have seen some towns arranged somewhat like this in real life that also lacked such additional crossings. Sweet cozy small town!