Sean,
You can upgrade remotely as along as the WM controller has access to an FTP or TFTP server where it can download the new image file. Example CLI output of upgrade options and TFTP upgrade below:
L3L_K2_U41_WM1#upgrade ? FILE Location of firmware image
usb1:/path/file
URL Location of firmware image
URLs: tftp://[:port]/path/file
ftp://:@[:port]/path/file
sftp://:@[:port]>/path/file
http://[:port]/path/file
cf:/path/file
usb:/path/file
L3L_K2_U41_WM1#upgrade tftp://10.67.51.99/WM3600-5.4.4.0-007R.img Running from partition /dev/mtdblock6
Validating image file header
Making file system
Extracting files (this may take some time).........................................................................................................................................................
Control C disabled
Version of firmware update file is 5.4.4.0-007R
Removing unneeded files from flash:/crashinfo directory
FPGA firmware version is already at version 1_26, no need to upgrade
PoE updates are handled via a patch file
Power Supervisor updates are handled via a patch file
Checking if boot sector needs to be upgraded
Boot Sector version 00008, image file bootsector ver 00008, no change required
Writing Kernel to /dev/mtd5
Writing BootOS to /dev/mtd16
Successful