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In terms of manpower, you can largely automate the sails today, though they do require maintenance. The issue is you basically need the same crew on a 20 TEU ship as a 20,000 TEU one, because you can’t safely operate with everyone asleep. Except sails scale in terms of surface vs drag scaling in part base on volume which makes mega sailing ships much more difficult.

Now these aren’t insurmountable issues on their own, but wind as supplemental power via kites or something seems like a far more viable option.

The discharging and loading of containers is already automated. Modern container terminals work almost completely autonomously. What specific automation did you have in mind to help with discharging/loading?

"1, I suppose."