So far as I know, the JetBook is using FBReader to read ePubs and FBReader reads the entire ebook into memory when it is first opened. This is why there is a long pause on open. So I'm not surprised that a 36 MB ebook fails (not enough memory). For CHM's on similar devices I have seen FBReader fail on 5-10 MB ebooks. I am a bit surprised that even a study guide is this large.
You could try splitting the epub into pieces. Since an ePub is just a ZIP, it is possible to do this manually by making multiple "exploded" copies (rename to .zip and unzip) and removing some of the files from each. I don't know if Calibre will then make them into good partial ePubs or not (because the .opf and .ncx files will be wrong unless you edit those too) - but it is worth a try.
Another possibility is using Calibre to convert from ePub to eReader, because eReader is using different Reader software (as is PDF). I'm not optimistic that a ~36 MB eReader will work though.
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