I'm trying to replicate the example above. I want the bottom of the letter to overlap the swoosh shape (like the R does in the example) and have the outline/offset path around the letter R to be transparent (the circled part in the example). Please help.
If I am understanding you correctly, you want this logo to be able to have a transparent background? Then the swoosh needs to be cut out of the swoosh itself. Has this been converted to outlines? If so, just use a pathfinder command and then you can delete the stroke of the R after you are finished.