For the recommendation actually put in the devguide, change 'random position' to 'position near but not at the top'.
https://docs.python.org/devguide/committing.html#news-entries ends with
"A nice trick to make Mercurial’s automatic file merge work more smoothly is to put a new entry after the first or first two entries rather than at the very top. This way if you commit, pull new changesets and merge, the merge will succeed automatically."

My main point was that the devguide a) recognizes that there is an issue and b) does not require strict date order. Merging items into the NEWS on a daily basis would keep approximate time order. Hourly merges would do even better.

This recommendation, however, is not very effective. It only only avoids conflict with another patch if the other person does not use the 'nice trick' but puts the news entry at the top. Unless one looks carefully, it does not help the problen of merging maintenance bugfix items into a default list that also contains enhancement news not in the maintenance list*. In fact, blindly putting an item between two news items rather than a header and one news item makes that conflict more likely.

* There have been times, like last Jan-Feb, when default only items dominated the default news list.