you pictures are just god awfully confusing, you have like 3 different catch cans under the hood and lines that don't appear to be connected to anything.
The lines from the block to the relocation kit, those go to the bottom of the sandwich plate/ so it looks like their going into the bottom of the oil filter.
The lines to the cooler go into the side of the sandwich plate. Pump cleaned oil through the cooler, not dirty.
with those lines/cooler, you're looking at like an extra 1-1.75 quarts of oil.
Just being honest, but running a line that long through the driver side... A bit ridiculous
