This type (2) of debugging is already implemented in the RT-SDK! And this was part of your Advanced SDK Training. (I assume you participated in the training, because this is the only way to get the RT-SDK).
You just build the example (e.g. automation.scheduler) and start the debugging. You can see this in the video attached. Of course breakpoints are hit here.
I would guess, that something in your scheduler configuration is not right. And thats why your callable does not get created. Please take a look at the scheduler configuration we provide in the samples or create a scheduler config on a ctrlX CORE (like I mentioned in the post above).
One additional information: Its not possible to debug samples which use the motion app via this way, because the motion-bundles are at the moment not included in the build-environment.
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