Hi Ken,
looking at the log output there are some warnings and errors:
(a) No license file found. Run in demo mode.
No license file found. Run in demo mode.No license file found. Run in demo mode.
--> you should consider to buy a license or your license file is not at the required place.
(b) Your input file is maybe not recognized
ERROR: unknown file format. file name '/Users/KenJacobMacbook/QGIS/LiDAR/lyons cutler/first returns'
--> please avoid spaces in the file path, ensure the file is really there
(c) Your input file is maybe too big
you try to process 74 million points.
las2dem64 is optimized for point cloud sizes up to 20 million points.
--> please use lastile64 before to tile your file into smaller tiles and use this files to create a DEM.
(d) The temp space can not be written
ERROR: cannot open file 'temp.32.00060.tmp'
Probably this error will disappear if (a)-(c) is solved. If not you can try to use "-temp_files /temp" as additional command argument to write the temp files to a non standard temp file location on your local drive. Please use a very simple location which sure exists. Optional you can probably configure wine to use another default temp directory which will be used.
Cheers,
Jochen @rapidlasso