> My understanding is that we walk first to last, and the last matching 
> configuration wins, and in theory that means the LocationMatch should win.
The last match doesn't win, it's merged on top of whatever the current
per-dir*per-module config is.

Just like a normal mod, whoever evaluates <if> (core) can decide to
replace/merge/append then act on that config later.
The merge for If sections encountered is to accumulate them in the
per-dir config. After all the other sections have been parsed, the
accumulated if sections are evaluated shortly after the traditional
location/dirwalk stuff.

sections.html does show <if> as evaluated last:
http://httpd.apache.org/docs/current/sections.html#merging

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