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A few people have mentioned this on the nexus: Leader requirement off, no problem to start the city plan, but no upgrade option unless you assign a leader (who you can unassign again after the upgrade is finished). I think this will work for ketrack, maybe it's something for kinggath to look into. Don't think anybody mentioned which Sim Settlement version they're using, though.
Hi. Long time listener, first time caller. I've noticed the option to upgrade is missing even with the Require Leader option is set to Off. However, it will upgrade automactically without a leader if that option is also turned on. I can confirm that the manual options is missing from the table when there isn't a leader, however.