-50 Error When Attempting to Sync

Hey all,
I've seen a few -50 error threads around, but they aren't very specific about the problem, or don't involve my problem. I'll be as specific as I can.
I receive the "The iPod cannot be updated. Unknown Error (-50)" message whenever I try to resync the iPod for a second time. The iPod syncs properly the -first- time, but any subsequent manual attemps to sync fail.
It does this whenever I do -anything-. Name change, remove files, add files (pictures, video, music). It applies too all types of legitimate filetypes read by the iPod (MP3, MP4, JPG).
The only way to get around it is to eject the drive, disconnect the cable, then reconnect the cable. But if I do that, it still won't -automatically- sync, I have to start iTunes (even though I have it set to start iTunes on dock).
I haven't tried anything yet, besides reinstalling iTunes. This is a problem that has followed me -from- iTunes 6.
I'm also fairly positive it has nothing to do with the iPod in question, because it is brand new. I received a replacement within the last two months (and that's how long I've had this problem).

Hey there,
I would try trashing the iPhoto Photo cache to the trash because it may be corrupt and see if that helps. Instructions on how to do this can be found in the Apple support document below. Hope it helps.
[Photo Sync creates iPod photo Cache|http://support.apple.com/kb/TS1314]
B-rock

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Runtime Errors         CONNE_IMPORT_WRONG_COMP_TYPE
Except.                CX_SY_IMPORT_MISMATCH_ERROR
Date and Time          19.11.2008 15:14:08
Short text
Error when attempting to IMPORT object "TS_CHECK".
What happened?
Error in the ABAP Application Program
The current ABAP program "SAPLSTD4" had to be terminated because it has
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Error analysis
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Missing RAISING Clause in Interface
Program                                 SAPLSTD4
Include                                 LSTD4U03
Row                                     1
Module type                             (FUNCTION)
Module Name                             DB02_ORA_FILL_TS_CHECK__CRITOB
Trigger Location of Exception
Program                                 SAPLSTD4
Include                                 LSTD4U03
Row                                     51
Module type                             (FUNCTION)
Module Name                             DB02_ORA_FILL_TS_CHECK__CRITOB
Source Code Extract
Line
SourceCde
21
DATA: BEGIN OF TD110.
22
INCLUDE STRUCTURE TD110_STRU.
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DATA: END OF TD110.
24
25
CURR_TIME = SY-UZEIT.
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CURR_DATE = SY-DATUM.
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CALL FUNCTION 'GET_DB_ORA_RELEASE'
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IMPORTING
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ORACLE_RELEASE = ORA_REL.
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IF FLAG_REFRESH = 'y'. FLAG_REFRESH = 'Y'. ENDIF.
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flag_refresh = 'Y': Es soll in jedem Fall auf die DB zugegriffen werd.
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CLEAR TS_CHECK. REFRESH TS_CHECK.
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CLEAR CRITOBJ. REFRESH CRITOBJ.
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CLEAR NR_CRIT_OBJ.
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IF FLAG_REFRESH <> 'Y'.
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Suche zunächst im Arbeitsspeicher !
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CLEAR TS_CHECK_CACHE. READ TABLE TS_CHECK_CACHE.
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IF NOT ( TS_CHECK_CACHE IS INITIAL ) .
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TS_CHECK[] = TS_CHECK_CACHE[].
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CRITOBJ[] = CRITOBJ_CACHE[].
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OK_1 = 'Y'.
47
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Suche danach in 'MONI' !
49
ELSE.
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PERFORM PREPARE_MONIKEY USING 2.
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IMPORT TS_CHECK CRITOBJ FROM DATABASE MONI(DB) ID MONIKEY.
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53
IF SY-SUBRC = 0.
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OK_1 = 'Y'.
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TS_CHECK_CACHE[] = TS_CHECK[].
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CRITOBJ_CACHE[] = CRITOBJ[].
57
ENDIF.
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ENDIF.
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'Same procedure' für datetime:
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IF NOT ( TD110_CACHE IS INITIAL ).
62
DATETIME-MONI_DATE = TD110_CACHE-DATUM.
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DATETIME-MONI_TIME = TD110_CACHE-UZEIT.
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ELSE.
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PERFORM PREPARE_MONIKEY USING 3.
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IMPORT TD110 FROM DATABASE MONI(DB) ID MONIKEY.
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IF SY-SUBRC = 0.
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DATETIME-MONI_DATE = TD110-DATUM.
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DATETIME-MONI_TIME = TD110-UZEIT.
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TD110_CACHE = TD110.
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This error occurs due a corruption in the table MONI.
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