I never played the first, but Settlers 2 was fantastic. I always preferred it to later installments because it had a strict grid of nodes, creating a complex graph of buildings and paths, rather than the more freeform pathing.

It was such a joy to grow the supply chains and deal with the all messy network logistics and bottlenecks. It sounds quite boring said out-loud, but we are in HN after all, I think you'll get it :)

Sounds like Transport Tycoon. I remember realising it said something about me that while my friends were building epic rollercoasters in Rollercoaster Tycoon I was much happier making train links between coal mines and power stations, creating a local and express rail serving linking a dozen cities…

Yes, S2 is still the best. Few years ago I finally finished all missions, the only thing missing is a more detailed story; but that's how it usually was in the 90s I guess.