My main concern has always been that, from a design perspective, a centrally-planned road/railway/etc. is almost always more effective (I'd be happy to be proven wrong) - it doesn't bob and weave unnecessarily around uncooperative actors (eminent domain), connects places that would, on their own, maybe not have the economic power to join such a project, provides standarised quality and safety.
Sure, private/local entities would cooperate to, for example, join two city-states together, but intuition tells me that a "grand plan" produces a more cohesive (and efficient) network.
Again, happy to be corrected by someone with experience (though I doubt there is a huge corpus of knowledge on decentralized infastructure planning).
this territory is moderated
Here's the biggest book I'm aware of on the subject. I'm familiar with the case the author makes but I haven't read the book. I probably should.
This isn't the source I was hoping to find, but it's an article that touches on the economic difference between the privately built and operated Great Northern Railway and it's subsidized competitors.
A general point I'd make about your intuition for planning is that it ignores tradeoffs. Having an optimal transportation network is not the highest end in the world and it's not at all unreasonable to route around things that have higher marginal value than reducing transit times slightly. It's really no different than the case against centrally planning anything else.
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