Thanks for sharing, very cool! Its cool that S1 has macro capability and able to put into the toolbar... That alone is worth the price of admission.
So you were not able to get the macro to set the duration of your keyswitches automatically, you have to apply them to staccato length as a separate manual step?
The main point of a VST is not to eliminate some of what you're doing with macros, you still need a way to add SOMETHING to the tracks that will indicate which articulation to play. But the point is that you can hide the details. instead of embedding keyswitches into the track, which are completely different for every library, you embed a single event per articulation.. this could be a program change, or a CC message, or an automation point, or could also be a single keyswitch event too if you want. Then in the VST you map each of those to perform during playback whatever you need to for each sample library. Some sample libraries need to be channelized, some need keyswitches, sometimes more then one keyswitch. Some combine both. And there are other interesting issues such as latency compensation between articulations with slow attacks and other factors like that. All of the details like that can be buried inside a "map" in the VST. Then all you have to do in the DAW is find some way to tell the VST at any given moment which articulation you want enforced. LogicPro does this by letting you assign an articulationID to each event. Cubase does this with Expression Maps, which I'm not much of a fan. DP provides nothing, S1 provides nothing. But with a VST, you could still at least use ProgramChange events or CC's or automation points, etc.. to be the indicator of which articulation to use...a single event presents a single articulation, even if inside the VST its doing more elaborate stuff, depending on the sample library being used. It keeps your tracks much more simple in the DAW. This also provides a way to use a consistent approach, in other words, you could have it so that PC1 always means staccato. Then in the VST you decide for each sample library how to map PC1 into whatever each sample library needs to play staccato. But in S1 you just always use the same PC1 for staccato. That's a simple example, but you get the point.
I have other more elaborate ideas for the VST which will expand what is possible when combining libraries, applying note expressions, automatically doing legato on the fly, etc.. Anything that reduces the need to manually massage the midi data on the track in order to get articulations. My dream is, I enter the notes, I quantize them to the grid, I put simple tags (as events) to indicate which articulation for each note or phrase...then let the VST humanize, legatoize, send keyswitches, channelize or whatever it needs to according to the sample library map defined within.