This post is a more ‘fleshed-out’ version of my response to a question posed by Gordon Maclean (http://www.onemanwrites.co.uk/), but the question is common: “Now that I know I want to, how do I move from an unstructured environment to a structured environment?”.  The Author-it team attend many conferences both in speaking capacities and as vendors.  We get the chance to talk to people from a huge range of organizations, from the battle-scarred people on the cutting edge to those who have only just started thinking about how structured content will benefit them.
The benefits of well structured content can be quantified very easily, especially when this discipline is applied to the broader organisation.  In almost all cases one of the biggest hurdles is working out how long (and how much) to get from where you are to where you want to be. Once the enthusiasm of DITA or custom schema dies down and people realize how much effort will be involved in migrating or re-writing existing content in order to comply, at the same time as meeting their day to day work requirements, the task has become huge and the true cost almost unknown.  Every hour that a team don’t spend writing (meetings, problem solving, struggling with a new tool, can’t publish the content, etc), every hour a developer spends updating a schema/specialisation/XSLT, every day a project slips, all add to the true cost of the project.  When management add this up the cost of tools is often minor in comparison.
According to our clients this has been the biggest gap - managing and evolving non-compliant Topics when the technology requires compliance to deliver an output - eg. the XSLT or DITA Toolkit chokes because your content isn’t yet fully compliant.  We talk to a lot of organizations migrating from Frame/RoboHelp/Flare (and even Word) and regardless of technology the big hurdle is the need to continue meeting deadlines while migrating from unstructured content to structured content.  For some it’s easier to draw a line under the current content assets and start from scratch.  This is a decision that effectively writes off all of the accumulated value of existing content - knowing this value, and the associated cost of migration, and deciding it’s cheaper to start again.
Not everyone can make that decision and so clients look for migration strategies that allow segmenting of content, evolution, and tools that support them during evolution.
In the 5.2 release of Author-it we’ve added template-based structured authoring where, once content is imported (or written), you can apply a DITA or other structure over the Topic and see exactly where you do and do not structurally comply.  Once your Framemaker or RoboHelp document is imported you immediately see which Topics are compliant and which are not, but you can still publish your document.  You can continue to meet deadlines and always have complete visibility of which Topics in which projects need to be updated to meet your structure standards.
The Author-it Structures are templates that can be applied to groups of Topics.  If you change the template, all Objects inherit the new structure rules (or show you they now fail to comply).  Workflow controls mean Topics *must* comply at certain Release States (’Draft’ can be non-compliant but ‘Released’ must be compliant), and Publishing Profiles remove all non-compliant topics during publishing if you plan to use the DITA Toolkit or similar XSLT processor.
You can check out my short video on structured authoring

Posted By: Matt Armstrong,Sales Director Asia Pacific, Author-it Software Corporation