I think it messes up when triggers are parented and perhaps it may be based on pre-set pushdir angles. So, while an angle like 0 0 0 will work and act normal, 0 180 0 won't while parented. When parented it will push at 0 0 0 angles regardless of the preset. When unparenting, it acts "normal" reverting back to the push angles but not where the trigger was last located. Otherwise, restarting the round fresh without touching anything acts normal.
Here's a screenshot of a push that will not push at the appropriate direction that it was compiled for.
I was able to confirm this by toggling triggerpushfix_enable and it does appear to be coming from the plugin.
Might be due to the fact that the plugin doesn't take into account parent rotations. Try using the version I've attached which uses m_angAbsRotation rather than m_angRotation and let me know if it works.