I left a few comments on rietveld,
In general, if making the doctest pass entails adding superfluous code (e.g. sorted(), <BLANKLINES>, #doctest: +SKIP (if visible), setups/teardowns, or even whole files) or removing details that might be useful (ids or filenames in reprs), I'd rather skip the snippet altogether.

Keep in mind that most of those snippets are there to document, not for testing, so imho the priority should be keeping them clear and to the point.
The behavior of those snippets should already be covered by unittest, so the only downside of skipping is that, if the behavior changes, the examples will be wrong until someone notices.

If others agree, this should make the patch simpler and easier to review; if not, breaking it down in 3-4 patches that address separate issue might also help reviewers.