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Why do you feel the need to wait for move_group to initialize everything?

Usually you should only need to wait for the respective ROS interface you want to use to come up. E.g., MoveGroupInterface proceeds that way: https://github.com/ros-planning/moveit/blob/b8b57846650f7662a44106e0b7728e0c9ca36888/moveit_ros/planning_interface/move_group_interface/src/move_group_interface.cpp#L151

If you really want to wait for the You can start planning now! message, you will have to either

1. modify move_group around here to publish to a latched topic, e.g., move_group/initialized or
2. write a new MoveGroupCapability that polls MoveGroupContext::status() and publishes said topic if it returns true.