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Preface: not my area of expertise, but your question intrigued me, so I tried an experiment.

I am on a Win 7 machine, using LibreOffice 4+ and Calibre. I had some large text documents that I used for the test. I created a two column table in LibreOffice and pasted the text files into the left and right cells. They expanded as necessary (16 pages). I saved as HTML. It looked OK in IE. I imported the book to Calibre and ran a conversion to epub using the defaults. The text on the right did not show up until about page 5 (white space until then). I don't know why.
As an initial demonstration, this may be helpful, but it obviously has issues, including those cited by Tom of paragraph alignment. A way to address the alignment might be to use multi row tables and keep the related text in the same row, different columns. A row could be as small as a paragraph, or as large as a chapter.

I also tried creating a two column frame, but that behaved like a newspaper set up, the text that was beyond the bottom of the first page wrapped to the second column, so that's not the way to go.

I thought about my test a little more and decided the text I used was not suitable. I tested again using the first 32 sonnets in the Complete Works of Shakespeare that I had as a text file. I put the same text into both columns, independently. I proceeded as above. After conversion it looked pretty good, but not perfect. The issues I noted were: the left column had about 4 lines of white space at the top, which the right column did not; the columns did not fully match throughout the epub of 41 pages, but were pretty close. This may actually meet your needs.


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