Hi Keith,
I can’t really see anything wrong in your logs.
The logs show two drives - sda is a ST3000DM001 which has a reserved (hidden partition) and a second partition sda2 that is mounting at /media/PiDisk1 at 19:52:41 in your log.
A second drive sdb is being mounted at /media/500gHDD at 21:35:41 in your log. (I assume this was plugged in later)
Both drives are getting samba shares created as expected using net usershare add:
Sep 29 19:52:41 osmc sudo[1120]: osmc : TTY=unknown ; PWD=/ ; USER=root ; COMMAND=/usr/bin/net usershare add PiDisk1 /media/PiDisk1 Auto-mount Volume osmc\osmc:f
Sep 29 21:35:41 osmc sudo[3973]: osmc : TTY=unknown ; PWD=/ ; USER=root ; COMMAND=/usr/bin/net usershare add 500gHDD /media/500gHDD Auto-mount Volume osmc\osmc:f
At 21:54:24 one of the drives is unplugged so it’s samba share is automatically removed:
Sep 29 21:54:24 osmc kernel: usb 1-1.2.3: USB disconnect, device number 19
Sep 29 21:54:31 osmc kernel: usb 1-1.2.3: new high-speed USB device number 21 using dwc_otg
Sep 29 21:54:31 osmc kernel: usb 1-1.2.3: New USB device found, idVendor=04e8, idProduct=6860
Sep 29 21:54:31 osmc kernel: usb 1-1.2.3: New USB device strings: Mfr=2, Product=3, SerialNumber=4
Sep 29 21:54:31 osmc kernel: usb 1-1.2.3: Product: SAMSUNG_Android
Sep 29 21:54:31 osmc kernel: usb 1-1.2.3: Manufacturer: SAMSUNG
Sep 29 21:54:31 osmc kernel: usb 1-1.2.3: SerialNumber: 4df196c90b749f65
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: USB disconnect, device number 21
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: new high-speed USB device number 22 using dwc_otg
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: New USB device found, idVendor=04e8, idProduct=6860
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: New USB device strings: Mfr=2, Product=3, SerialNumber=4
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: Product: SAMSUNG_Android
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: Manufacturer: SAMSUNG
Sep 29 21:54:33 osmc kernel: usb 1-1.2.3: SerialNumber: 4df196c90b749f65
Sep 29 21:57:02 osmc kernel: usb 1-1.2.4: USB disconnect, device number 20
Sep 29 21:57:02 osmc udisks-glue[354]: Device file /dev/sdb1 unmounted from /media/500gHDD
Sep 29 21:57:02 osmc udisks-glue[354]: Device file /dev/sdb1 removed
Sep 29 21:57:02 osmc sudo[4560]: osmc : TTY=unknown ; PWD=/ ; USER=root ; COMMAND=/usr/bin/net usershare delete 500gHDD
Sep 29 21:57:02 osmc sudo[4560]: pam_unix(sudo:session): session opened for user root by (uid=0)
Sep 29 21:57:02 osmc udisks-glue[354]: Device file /dev/sdb removed
Sep 29 21:57:02 osmc ntfs-3g[3965]: Unmounting /dev/sdb1 (500gHDD)
Sep 29 21:57:03 osmc sudo[4560]: pam_unix(sudo:session): session closed for user root
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: USB disconnect, device number 22
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: new high-speed USB device number 23 using dwc_otg
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: new high-speed USB device number 24 using dwc_otg
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: New USB device found, idVendor=04e8, idProduct=6860
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: New USB device strings: Mfr=2, Product=3, SerialNumber=4
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: Product: SAMSUNG_Android
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: Manufacturer: SAMSUNG
Sep 29 21:57:05 osmc kernel: usb 1-1.2.3: SerialNumber: 4df196c90b749f65
In fact it looks like multiple devices including a Samsung phone were disconnected at that point - did you unplug an entire USB hub ?
So I can’t really see anything wrong here assuming the latter disconnection was intentional. When you connect to the Pi using Windows explorer you should be seeing an “osmc” share which goes to the osmc home directory on the SD card, but you should also see shares called PiDisk1 and 500gHDD.
I would try browsing to the Pi from another computer if you have access to one.