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Don't try to figure OpenRoads out on your own.  Back in the InRoads/GEOPAK days, reverse engineering blew budgets and schedules.  The OpenRoads platform is dramatically more complicated, and the risk correspondingly worse.

• Talk to a real live person who has been through what you're planning to do.
  • If you're part of a mega-organization - find your colleagues who have already been there
  • find outside experts
    • online communities, user groups, etc.
    • talk to consultants

Never wait to get training.  Training is available right now.  While there is high value in in-person or live training, most of you can get what you need for free right now.

• If you own Bentley software, you likely have access to their LearnServer (learn.bentley.com).  Their offerings aren't perfect, but they're in easily-consumable short lean modules.  They typically have a downloadable training manual, exercises, and videos of the exercises.   They're updated pretty regularly.  
  • this should be your default training source, unless you have access to customized training.

Twenty five years ago, I authored my take on InRoads and InRoads Drainage training.  This time around, I don't see the point.  Bentley's LearnServer is my starting point for understanding and keeping current with the software;  I recommend it be yours, too.

• There are gaps, and that is my focus as an author and consultant.

YouTube: there's a lot of good content.

Communities:  Communities.Bentley.com is your primary support resource.  There is good value in their forums and their Knowledgebases (often found via Google search easier than an in-communities search).  You can ask questions there, and generally another user will provide answers in a day or two. 

Service Ticket: Connect.Bentley.com You pay for Bentley to respond to Service Tickets.  They may not resolve your issue, but they're respond to you.  Expect a day for someone to ask for more information - so try to be as explicit as possible (dgn's, pictures, step-by-steps, video).

Bentley is a business.  You pay them for support.  Support resources cost them money.  They are trying to provide "sufficient" support for as little money as possible - that's how business works.  Is it working for you?

If the support is inadequate, express that to Bentley via all the channels you can.

Bentley, like many large organizations, has formal systems of tracking and addressing issues.  "If it's not in the system, it doesn't exist".  Get it in their system.

• Log problems (via Service Ticket: Connect.Bentley.com)  It consumes time, but the fixers respond to noise - in the system.  Bugs need to be logged, and the more people logging an issue (and the bigger the organization logging it), the more likely it will be fixed (depending on a dozen other factors).
• Log enhancements.  The OpenRoads Ideas Portal is where Bentley tracks enhancements requests.  You can "Vote" for existing requests or log your own.
• Bentley polls their accounts as to their level of Satisfaction.  Make sure whoever is filling out the survey is aware of your level of satisfaction.