Unable to Print/PDF Plan Sheets in OpenRoads Designer

I am new to ORD and Microstation Connect. I am coming from V8i SS4/SS10. I am having issues trying to plot/print/pdf sheets in ORD 10.10

So I am trying to use print organizer with ORD 10.10. It lets me add the print files and it seems to recognize the print area and everything. However, when I go to print preview, the plan sheet shows up blank. When I try to plot/print, It tried to print the first sheet and then the print dialog box closes. The exception in the message center shows "Exception Encountered Inside [WorkerMicroStationProxy.Print]". 

When I try to print with Microstation Connect, my sheets are printing but my sheet views are not working (you can scroll down on this thread and see the Container File Live Nesting Issue I was having).

Can anyone please guide me why ORD 10.10 is not letting me pdf sheets?

Thank you so much in advance!

Edit: Adding that I am working in Projectwise.