Ah, I overlooked something. I usually have one track per instrument loaded with all the articulations I need for that particular instrument. Basically, I would open my sample library engine (Halion SE in this case), as an Instrument Track (no multi-out) load all the articulations I need and assign them their own MIDI channel. Then I would load the Expression Map into that track and then draw the articulations in the Key Editor as you did on that bottom image on your first post.
The way you have it set up, with multi-outs, would be more beneficial if you plan on using different instruments rather than different articulations of the same instrument (in this case, a Piano). Or if you’re using drums, which is a collection of instruments itself. But for a single instrument, such as a Piano, I would load it up the way I described above.
Try that and let me know if it works that way.