In my experience, lack of planning and docs strictly reduces liberty, because everyone is afraid to do anything but the most conservative thing, even when more radical work is clearly needed.
Matches my experience. I've lost count of the number of times I've seen people ask "why did they decide to do it this way" or "does this value in the test meet some requirement, or is it a bug?", without finding an answer because it is not documented and whoever did it left the company years ago.