Presumably there’d be regular missions, so there’d be relatively little additional planning for a given moon trip, similar to how there’s a lot less planning/paperwork that goes into a Falcon 9 launch these days than there was for any rocket before Falcon 9.

Starship’s goal is to drop cost of mass to orbit by a couple of orders of magnitude, if they pull that off, it would drop the cost of supporting a colony by quite a bit.