Firstly, I would use relative midi from KM to control the volume slider, via Logic's Controller Assignments window. Secondly, if you want to do something repeatedly while you hold a hotkey, take a look at THIS as a starting point.
Side-note, if you have an endless encoder, you can try using this rather than KM; a nicer experience, perhaps. Personally, I use a nObcontrol with a Stream Deck and I think it's an awesome combo.
Here's a quick macro that sets the selected note's duration to 1/16th, which should get you started:
Selected Note - Set Length to 16th.kmmacros (44 KB)
Forget about Logic "remembering" where the playhead has been and do this instead:
Either set your locators to the length you'd like to crop the region to or use the marquee tool to make your selection. Then use Logic's Crop Region outside Locators/Marquee Selection function. Personally, I prefer the marquee tool, as I have it bound to my right mouse button, so it's just a single click-drag-release and then one hotkey.