I loved all these games as a kid and I'm 25. I played it on my DS and had Widelands on my computer.

The artificial constraint of building roads with little people acting as relays holds up today because it makes the graph theoretic nature of the problem apparent to a 10 year old.

I can intuitively see flow and choke points in a way most games don't allow. I will see a pile of junk stacked up on a given node if my road network sucks. I often attempted to build more roads. I thought it was cool seeing how stuff moved through a network.

To contrast Rimworld, I needed a theoretical understanding of graphs before I could mentally model goods' flow between raw production, storage, and secondary production. Otherwise people would just walk long distances and everything would feel slow without understanding why. I did not understand the benefit of a relay system until hundreds of hours in.

That isn't to say Settlers 1 and 2 are perfect. The lack of in-game help and tutorials killed my progress past a certain point. You will probably need to help your kid.