I have a partial answer. If you would like to give one of your user roles basically-free rein with Learndash what I did was first, from the WP Backend Menu go to Settings > User Role Editor. Then select Additional Modules from the tabbed options at the top of the page, then, under the first list of options (prior to “Content editing Restrictions” check on the option “Activate per plugin user access management for plugins activation” (1.png). From here go back to URE @ Users > User Role Editor. Once here select “Plugins” from the options menu at the right of the screen (2.png). A modal will pop up allowing you to select the plugins that you would like for your specified role to manage (3.png and 3_details.png). From there, open up another browser and test your user’s WP backend experience and you’ll see that they now have mostly full control of your elected plugin (4_EDU-Dir_role_view.png).
With all of that being said, I’m still having difficulty in exacting the specific level of control that I would like to give these roles. The issue that I’m having is that no matter how granular I get with these options and how many I enable for my desired user there option set is still significantly diminished compared to mine. I’m not able to give them the Overvew, Reports, Add-ons, or Settings feature like I really want so that they can completely manage it on their own. I’ve spun my wheels for an excessive amount of time already, trying to figure out how to model these user roles exactly as I would like.
I hope that this helps, and pardon the lack of screenshots (as I had intended), I see that there is no way of uploading supporting images to this text. Also, if anyone knows how to solve the rest of the problem it would be great.