Instead of a text based-configuration file system, like the .ini's and .xin's of yore (they were easy to build tools for), it's "in the dgn" and multiple levels deep.  

I remember in 1999, pushing San Diego's support team to use the "Five-level System" to manage the the configuration of multiple departments across the City.  Many of the CAD Managers felt that five level was four levels too many.  While it was designed for "Distributed Simplicity" it was still "too complicated".

Twenty-five+years later, OpenRoads configuration is by far the hardest part of the platform.

1. It's the most complicated scope of anything I've seen in 35 years of using Civil software (three vendors). By far.
2. It's time-consuming.  You're opening and closing dgn files one at a time. It's SLOW.
3. It's really specialized and non-intuitve.  If you don't do something frequently, you have to re-learn it.  
4. It's never been fun and it's a whole lot less fun now.

5. Take care of your staff.

A primary reason it has taken many DOTs many years to develop a working workspace is that they follows Bentley's model.  Bentley's workspace development was driven by the demo jocks (God bless them).  Photo-realistic integrated 3D shop drawing -precision made excellent demonstrations.  And because Bentley modeled seven hundred drainage inlets and endwalls, EVERYBODY thought they had to model EVERY SINGLE STRUCTURE in their spec book.  They'll never get those years back.

What they needed to do was model a representative subset that covered the needs of the design, quantity and quality (spatial class detection), and contract needs.  Being able to see through the inlets curved grates, was cool, but it was never necessary.  It still isn't.