TJ, all your /dev/bus/usb/*/* files including the one for the printer
have "vm" group ownerships. Probably VMware or some other virtual
machine software is overriding the UDEV rules which set the group
ownership of the printer's file to "lp". So HPLIP (the preferred CUPS
backend for your printer) cannot access the printer and your job hangs.

Report a bug against your virtual machine software.

-- 
Printer (HWModel Name) May Not Be Connected
https://bugs.launchpad.net/bugs/348316
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