Please post links (or just attach them) to your results instead of inlining them, Drib's moderating broom swiped your images before I could take a look at them

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Not sure why you're using a few different softwares, so let's say if you were using GIMP all along:
* Crop/Compose/Scale
* Greyscale
* Remap to eInk palette w/ FS dithering
* Re-Greyscale [by which I mean Image > Mode > Greyscale] (might be important, otherwise the PNG is saved as a 16c, not 8-bit, which upsets some FW versions).
* Save as PNG
Also, unless you have some very specific needs, I'd recommend playing with the levels in a real colorspace, *before* greyscaling everything.