So, this subclass generates Wounds by doing melee damage. Does that also apply to damage done when performing Flagellant's Path?

 

Does the same apply for any other movement abilities, for example such as Leap from Bounding Boots?

 

Last but not least, does the Wound bonus from Tuotilo's Palm work the same way on a Shattered Pillar as any other Monk subclass?

You can get wounds from Torment's reach, so i would assume you can get them from Flagellant's Path, it's not exactly exploity though since they cap at 5 wounds.

 

Not sure about Tuotilo's Palm or Bounding boots.