Here's the small debug log. Sent 8 random sci-fi books. Failed at sending the 6th. While the 6th book according to Calibre companion and Calibre actually did sync, there are only 5 books in the books folder (using file explorer) but there are 6 covers in Calibre Companion.
Spoiler:
calibre Debug log
calibre 0.8.64
Darwin-12.0.0-x86_64-i386-64bit
Darwin
('Darwin', '12.0.0', 'Darwin Kernel Version 12.0.0: Sun Jun 24 23:00:16 PDT 2012; root:xnu-2050.7.9~1/RELEASE_X86_64')
Python 2.7.3
OSX: ('10.8', ('', '', ''), 'x86_64')
Starting up...
SMART_DEV ( 0.00: 0.001) startup_on_demand try port 28293
SMART_DEV ( 1.04: 0.818) startup_on_demand listening on port 28293
Started up in 10.44 seconds with 275 books
SMART_DEV ( 19.78: 18.687) reset
SMART_DEV ( 19.81: 0.000) set_progress_reporter
SMART_DEV ( 19.84: 0.000) open
SMART_DEV ( 19.87: 0.002) _call_client GET_INITIALIZATION_INFO
SMART_DEV ( 20.07: 0.172) open selected formats [u'epub', u'mobi']
SMART_DEV ( 20.10: 0.000) card_prefix
SMART_DEV ( 20.18: 0.052) set_progress_reporter
Job: 1 Get device information started
SMART_DEV ( 20.21: 0.000) get_device_information
SMART_DEV ( 20.24: 0.001) _call_client GET_DEVICE_INFORMATION
SMART_DEV ( 20.32: 0.028) _call_client SET_CALIBRE_DEVICE_INFO
SMART_DEV ( 20.41: 0.057) card_prefix
SMART_DEV ( 20.45: 0.000) free_space
SMART_DEV ( 20.49: 0.001) _call_client FREE_SPACE
DeviceJob: 1 Get device information done, calling callback
DeviceJob: 1 Get device information callback returned
SMART_DEV ( 20.61: 0.090) set_progress_reporter
Job: 2 Get list of books on device started
SMART_DEV ( 20.64: 0.000) books None
SMART_DEV ( 20.68: 0.002) _call_client GET_BOOK_COUNT
SMART_DEV ( 20.71: 0.007) books carda
SMART_DEV ( 20.75: 0.000) books cardb
DeviceJob: 2 Get list of books on device done, calling callback
SMART_DEV ( 20.79: 0.011) set_plugboards
DeviceJob: 2 Get list of books on device callback returned
SMART_DEV ( 20.95: 0.124) set_progress_reporter
Job: 3 Send metadata to device started
SMART_DEV ( 21.00: 0.002) sync_booklists collection attributes [u'']
DEBUG: 0.0 Starting get_collections: on_connect
DEBUG: 0.0 Renaming rules: {}
DEBUG: 0.0 Formatting template: {value}{category:| (|)}
DEBUG: 0.0 Sorting rules: []
SMART_DEV ( 21.07: 0.001) _call_client SEND_BOOKLISTS
SMART_DEV ( 21.14: 0.034) card_prefix
SMART_DEV ( 21.18: 0.000) free_space
SMART_DEV ( 21.21: 0.002) _call_client FREE_SPACE
DeviceJob: 3 Send metadata to device done, calling callback
Job: 1 Get device information finished
No details available.
Job: 3 Send metadata to device finished
No details available.
Job: 2 Get list of books on device finished
No details available.
DeviceJob: 3 Send metadata to device callback returned
SMART_DEV ( 21.33: 0.083) _call_client NOOP
Job: 3 Send metadata to device finished
No details available.
SMART_DEV ( 31.40: 10.032) _call_client NOOP
SMART_DEV ( 33.47: 2.033) set_progress_reporter
Job: 4 Upload 8 books to device:Eternity, The Venging, Vitals, The Wind From a Burning Woman: Six Stories of Science Fiction, Slant, Strength of Stones, Quantico, Queen of Angels started
SMART_DEV ( 33.49: 0.000) set_plugboards
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: Eternity at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/vt5OkMcaltmpfmt.epub
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: The Venging at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/wi7dwhcaltmpfmt.epub
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: Vitals at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/RGI0sQcaltmpfmt.epub
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: The Wind From a Burning Woman: Six Stories of Science Fiction at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/2hEqSlcaltmpfmt.epub
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: Slant at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/lxUotccaltmpfmt.epub
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: Strength of Stones at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/5js5wEcaltmpfmt.epub
Device using plugboard epubControlError(None,)
Traceback (most recent call last):
File "site-packages/calibre/gui2/device.py", line 83, in run
File "site-packages/calibre/gui2/device.py", line 478, in _upload_books
File "site-packages/calibre/devices/smart_device_app/driver.py", line 43, in _synchronizer
File "site-packages/calibre/devices/smart_device_app/driver.py", line 749, in upload_books
File "site-packages/calibre/devices/smart_device_app/driver.py", line 409, in _put_file
File "site-packages/calibre/devices/smart_device_app/driver.py", line 376, in _call_client
ControlError: <unprintable ControlError object>
SMART_DEVICE_APP None
Setting metadata in: Quantico at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/tS_qeMcaltmpfmt.epub
Device using plugboard epub SMART_DEVICE_APP None
Setting metadata in: Queen of Angels at: /var/folders/p_/ydw8nrsd7jq1yvwr5kyzdzqh0000gn/T/calibre_0.8.64_tmp_ehwn_l/xShHz1caltmpfmt.epub
SMART_DEV ( 34.52: 0.990) upload_books [u'Eternity - Greg Bear_454.epub', u'The Venging - Greg Bear_449.epub', u'Vitals - Greg Bear_450.epub', u'The Wind From a Burning Woman_ Six Stories of Science Fiction - Greg Bear_451.epub', u'Slant - Greg Bear_447.epub', u'Strength of Stones - Greg Bear_448.epub', u'Quantico - Greg Bear_445.epub', u'Queen of Angels - Greg Bear_446.epub']
SMART_DEV ( 34.56: 0.005) _put_file Eternity - Greg Bear.epub 580027
SMART_DEV ( 35.86: 1.276) _call_client BOOK_DONE
SMART_DEV ( 35.91: 0.011) _put_file Venging, The - Greg Bear.epub 209977
SMART_DEV ( 36.36: 0.419) _call_client BOOK_DONE
SMART_DEV ( 36.40: 0.009) _put_file Vitals - Greg Bear.epub 330370
SMART_DEV ( 37.07: 0.635) _call_client BOOK_DONE
SMART_DEV ( 37.11: 0.010) _put_file Wind From a Burning Woman_ Six Stories of Science Fiction, The - Greg Bear.epub 227956
SMART_DEV ( 37.84: 0.698) _call_client BOOK_DONE
SMART_DEV ( 37.89: 0.010) _put_file Slant - Greg Bear.epub 389416
SMART_DEV ( 38.65: 0.735) _call_client BOOK_DONE
SMART_DEV ( 38.70: 0.010) _put_file Strength of Stones - Greg Bear.epub 202215
SMART_DEV ( 39.03: 0.298) _call_client device went away
DeviceJob: 4 Upload 8 books to device:Eternity, The Venging, Vitals, The Wind From a Burning Woman: Six Stories of Science Fiction, Slant, Strength of Stones, Quantico, Queen of Angels done, calling callback
DeviceJob: 4 Upload 8 books to device:Eternity, The Venging, Vitals, The Wind From a Burning Woman: Six Stories of Science Fiction, Slant, Strength of Stones, Quantico, Queen of Angels callback returned
SMART_DEV ( 39.08: 0.018) post_yank_cleanup
Job: 4 Upload 8 books to device:Eternity, The Venging, Vitals, The Wind From a Burning Woman: Six Stories of Science Fiction, Slant, Strength of Stones, Quantico, Queen of Angels finished
ControlError(None,)
Traceback (most recent call last):
File "site-packages/calibre/gui2/device.py", line 83, in run
File "site-packages/calibre/gui2/device.py", line 478, in _upload_books
File "site-packages/calibre/devices/smart_device_app/driver.py", line 43, in _synchronizer
File "site-packages/calibre/devices/smart_device_app/driver.py", line 749, in upload_books
File "site-packages/calibre/devices/smart_device_app/driver.py", line 409, in _put_file
File "site-packages/calibre/devices/smart_device_app/driver.py", line 376, in _call_client
ControlError: <unprintable ControlError object>