Still not detecting, or at least the Send to Device isn't lighting up. Here's the output from the debug command you game me above. Thanks!
C:\Program Files\calibre>calibre-debug -d
USB devices on system: [u'usb\\root_hub&vid8086&pid2830&rev0002', u'usb\\root_hu
b&vid8086&pid2832&rev0002', u'usb\\root_hub&vid8086&pid2835&rev0002', u'usb\\roo
t_hub&vid8086&pid2831&rev0002', u'usb\\root_hub&vid8086&pid2834&rev0002', u'usb\
\root_hub20&vid8086&pid283a&rev0002', u'usb\\root_hub20&vid8086&pid2836&rev0002'
, u'usb\\vid_0458&pid_0101&rev_0100', u'usb\\vid_045e&pid_00e1&rev_0007', u'usb\
\vid_046d&pid_c251&rev_0100', u'usb\\vid_05a9&pid_2640&rev_0100', u'usb\\vid_05a
9&pid_2640&rev_0100&mi_00', u'usb\\vid_0a5c&pid_4500&rev_0100', u'usb\\vid_0a5c&
pid_4502&rev_0100', u'usb\\vid_0a5c&pid_4503&rev_0100', u'usb\\vid_1949&pid_0002
&rev_0100', u'usb\\vid_413c&pid_8126&rev_0367']
Drives detected:
(ID, Partitions, Drive letter)
IDE\DISKST9160823ASG____________________________3. ADD___\5&94F7FCB&0&0.0
.0
('USBSTOR\\DISK&VEN_KINDLE&PROD_INTERNAL_STORAGE&R EV_0100\\B002A1A090623
900&0', 1, u'E:\\')
Looking for PRS500
Looking for PRS505
Looking for PRS700
Looking for CYBOOKG3
Looking for KINDLE
Looking for KINDLE2
Device Connected: <class 'calibre.devices.kindle.driver.KINDLE2'>
Trying to open device...
Total space: (1594953728, 0, 0)