tl;dr: Like footnotes, but on the side (easy part). These notes must be on the same page as their reference points, so the "main text" needs to break whenever the notes break.
I'm trying to produce something like this:
I've been using memoir. Here's an idea I had. My understanding is that \footnote creates a float that tries to place itself at the bottom of the nearest page. Would it be possible to place the "footnote anchor" elsewhere? For example, with some interesting page geometry, something like this:
The difficult part is in the question title: ensuring that page breaks respect the column-column alignment.
Here is a MWE.
\documentclass{memoir}
% geometry stuff here
\begin{document}
Blind Text
Lorem ipsum dolor sit amet. \columnnote{This is the first ``footnote.''}
The quick brown fox jumped over the lazy dog. \columnnote{This is the second ``footnote.''}
\end{document}



paracol, but that still leaves the page breaks to be dealt with. – Simon Kuang Aug 04 '15 at 21:59memoir'ssidebarhas the vertical alignment right, but it doesn't create page breaks that keep the\sidebarcommand's context and the actual sidebar on the same page. – Simon Kuang Aug 05 '15 at 18:30\sidefootnoteand\sidebarmight do the trick except for the page breaking requirement which I think is possible but devily hard. – Peter Wilson Aug 06 '15 at 19:30\sidebar. So far I think the most viable solution will be to require a double compilation in which the first compilation hooks shipouts to determine ideal break points (viz. with a per-sidebar incrementing counter)---definitely not impossible ... – Simon Kuang Aug 06 '15 at 20:32