Nice to have a fellow-traveller in the DAW world. I was a Cakewalk user since way back in Pro Audio 6 and even before, but I always felt like I was fighting the program. I'm sure it was a much me as any flaw in Pro Audio/Sonar. It just seemed like a lot of things were needlessly difficult. Anyway, the superior Score View and the special handling of articulation switching available in Cubase had great appeal to me, even seemingly small things like track subfolders and easier work in drawing and editing controllers. My initial work in Cubase has only confirmed what my instincts and the Trial Version told me. Cubase is just a better-conceived product for someone like me who works exclusively with MIDI orchestration.
Regarding the MIDI track output selection, I have a Strings instance of VE Standard set up and loaded. Since all the channels were set to MIDI input "All" (that's how I have been working to this point), I changed one to port "1" and another to port "2" so I had two VE MIDI input ports ready. I do know how to select the MIDI track outputs in Cubase, but when I go there hoping to see different ports available for selection, i.e. Vienna Ensemble (instance 1 port 1, instance 1 port 2, etc, I don't see them. All I see is Vienna Ensemble (Instance 1), Vienna Ensemble (instance 2), etc. I'm wondering if there is some setup needed in Cubase that I don't know about. I've looked for it, in the manual and on the web, but I can't find anything.