I've used a workflow of Indesign export to epub-->edit in Sigil-->convert to Mobi using the Kindle-supplied KindleGen or—even better, and in my experience no different from the result with KindleGen, simply opening the epub file directly into Kindle Previewer for Mac (it seems to have KindleGen built right in). I've never experienced the issue with jpegs that you report. However, the size works best if you specify the height and width in the tag. Good luck.
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