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You're in an awesome position -- the product is a server which means you can do anything you want with the docs. Here are a few things users are starting to consider... In the not too distant future they might become expectations:
* Social input -- Both in the private group (behind the firewall) and the outside world
* Responsive design -- Format according to device (tablet, phone)
* Adaptive content -- Filter content by device, user profile, product constellation, context
* Dynamic content -- Bring in live data from the product state or from supporting data sources
* Cherry picking -- Assemble a custom set of topics
This is on top of the usual suspects such as a TOC, search index, glossary, links, context-sensitive (well, context-specific) calls, media, etc.
My product is similar, and I'm lucky enough that the company let me invent my own system. I deliver raw DITA, and convert it to HTML on the fly. This gives me room to inject things dynamically at the last minute. At this time I can:
* Filter by user type
* Convert printable content into HTML forms -- I do this for the API docs
* Call the product API to inject real-time data
I'm working on other capabilities according to time and need. And yes, we still ship a PDF, so single-source turns out to be a requirement.
But the point is, get ready for a quantum jump in user expectations.
Doc-To-Help 2014 v1 now available. SharePoint 2013 support, NetHelp enhancements, and more. Read all about it.