Hi dschaefer, I just went through the process of adding a logo for my board on PCB Designer 16.0. Here were my steps (after much web research, and some trial and error):
1) Took a picture of what I wanted to make a logo of (a propeller in my case).
2) Imported the picture into a DWG drawing tool (I used DraftSight, which is free).
3) Traced the outline of the propeller over the photo with a polyline. Added some circles. Exploded the polyline into a bunch of tiny lines (polyline didn't import into PCB designer). Deleted the photo.
4) Saved drawing as an ASCII .DXF file.
5) At this point, I was unable to import the DXF into my board design directly, so start a new file in PCB designer. Drawing type: mechanical symbol. Import the DXF (File->Import->DXF...
6) For my logo, after import, a part of the logo was cut off, and the only way I could figure out how to get it all was to resize the page larger (Setup->Design Parameters->Design) after importing, and then import the logo again, with the 'incremental addition' check box checked in the DXF import window.
7)Once the logo is all in there, and saved as a .DRA file (in the folder with all the other DRA files), go back to your design. Select Place->Place Manually. Go to the Advanced tab, and make sure the 'library' box is checked. Go back to the Placement List tab, and from the drop down select Mechanical Symbols. Your symbol should be there. Check the box beside it and place the logo.
This process worked for me, hope it works for you.