There are variuous kinds of documents and out goal is ensure that they stay in step with the code. I design development processes to encourage the well-intentioned, if forgetful, developer to do it right. So whereever possible I want the documentation to be "naturally" in step with the code, developer updates code, they with little effort can update the docs - try to reduce the number of context switches. Also note that much of what I propose natually associates a version of the docs with a version of the code. Using a good SCM we can get back to any version of the docs.
So let's look at some documentation types.
First, the API docs. I am a library (or sub-component) author. I make some changes to the API, add new parameters, add new methods. If the documentation is extracted from comments in the code then as I'm visiting the signature of the methods, and the Class declaration I can see the documentation. MY OCD kicks in and I update the docs. Painless, doesn't add much time. The build process extracts the docs job done. See java's JavaDoc approach for an example, but I've been doing this long before Java came along, it's not a new technique.
Now what about the conceptual, structural docs. Again where possible I favour extarcting that from the code. So I treat "Master" classes, or main entry points as worthy of extra documenation. If necesseray I including an overview JavaDoc perhaps at the package level. Now clearly more discipline is requried to update those docs, but as the same technique is usde for capturing them the inertia of "don't want to launch the workd-processor" is overcome.
Tutorial information: how about using some of the tests as living examples. The code must update the test (you do Unit Test, right?) So, annotate some key tests with explanations. Now if the API has changes that test code must change, and while we are there we update the docs.
That leaves large scale documents such as the archiectural overview, deployment topologies etc. Well there we just need to be disciplined. We're mature architects, so we just do the job!