<quote name="Jared Zimmerman" date="2014-03-28" time="22:52:24 -0700">
"For what it's worth" Its not worth much to anyone if you don't suggest a fix, or let us know why it was an issue for you. :)
Yeah, as I was laying down for bed after sending this (I felt sick yesterday) I thought how my message was only 25% worth it :)
So, why:
Because the numbering helps me quickly scan pages like: https://www.mediawiki.org/wiki/Wikimedia_Release_and_QA_Team
Since TypoRefresh is gone from mw.org, see: https://en.wikipedia.org/wiki/User:Greg_%28WMF%29/Example
And now I can't easily find the other pages that looked bad for me because TypoRefresh isn't there (all on mw.org...) But basically any pages that heavily use outlines (3 or so levels deep), like is common on documentation/work pages (not as common on encyclopedia articles). Sphinx (the python doc generator) does the same, see eg: http://docs.python.org/2.7/library/index.html
Even the PHP manual gives you a visual anchor (the bullet): http://www.php.net/manual/en/
Summary: When there are many sub-sections listed on a page, it causes the TOC to have a ton of sub-bullets. The human eye (at least mine, and I think others based on some of the feedback on this) likes to have something to hold on to as it scrolls down (bullet, number, something) not white space, so that it doesn't lose/forget which level of indentation it was it. To wit: I find myself very confused when looking at eg the Rel&QA team page above because of the lack of grounding on the left.
Because of that, I'd strongly advice against the TOC change be included on mw.org since mw.org is definitely in group A (docs) not group B (encyc).