So it might have been caused by the .ash script.
This is the main culprit - mostly switching into the war hippy outfit and back again.
http://kolmafia.us/showthread.php?960-One-Click-Wossname-automatic-level-12-quest-completion
There was no problem on my previous ascension with this script and the vanilla v15.0 kolmafia.
This script would call these functions (and fail to change gear correctly)
outfit("current");
outfit("War Hippy Fatigues");
The session log doesn't show any error after these lines, but the resulting adventure attempts failed (going places that required War Hippy Fatigues did not work after War Hippy Fatigues were apparently equipped)
I'll definitely retest whenever I am able.