Let me try and improve this situation for you, at least a little bit.
First off, you want to enable the Transcription Playhead to get your dynamic marker functionality. On the Mac, you can toggle this using ⌘T (or assign a MIDI command to it.) Each time you press the play button, it will start from wherever the Transcription Playhead is located.
Unfortunately, I don’t think you’ll be able to execute these actions right now exactly as you have them configured[1]. That’s why I’m (very slowly, carefully) overhauling of this important aspect of Capo’s feature set. When I (eventually) get done with this, you should be able to set it up how you describe above.
Long story short: Capo’s current MIDI implementation is very simple. It ignores message values, so the sustain pedal on/off won’t get treated differently from one another.
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