Hi Aaron,
I think I am pretty much in the same place (except I’ve not added any custom buttons). It does make more sense, I think, to have the response & context in the post content. Your manual method might be the sanest long term, avoiding technical debt. The IndieBlocks plugin does this too as it put everything in the post content. The link to David’s post is hopeful. I am guessing there is probably a clever way of moving the responses into the content on old post, but it would be way beyond me.