Sync not syncing playlists correctly

New user. Ran into considerable problems syncing with itunes before discovering the ipad doesn't support playlist folders so I created new playlists not in folders and tried syncing them over usb. itunes shows it has synced everything, but from the ipad while the songs and playlist titles are synced, the playlists contain no songs. If I add the songs to the playlist on the ipad they work, but if I sync those, it deletes the playlist contents on the computer. The same process works with a 3rd gen ipod with playlist folders. I have a window 7 64bit computer, itunes 10.6.1.7, and ipad 3 and rebooted the ipad. All sync tests report success. Diagnostics below.
Microsoft Windows 7 x64 Home Premium Edition Service Pack 1 (Build 7601)
Hewlett-Packard HP Pavilion g6 Notebook PC
iTunes 10.6.1.7
QuickTime 7.7.2
FairPlay 1.14.37
Apple Application Support 2.1.7
iPod Updater Library 10.0d2
CD Driver 2.2.0.1
CD Driver DLL 2.1.1.1
Apple Mobile Device 5.1.1.4
Apple Mobile Device Driver 1.59.0.0
Bonjour 3.0.0.10 (333.10)
Gracenote SDK 1.9.5.502
Gracenote MusicID 1.9.5.115
Gracenote Submit 1.9.5.143
Gracenote DSP 1.9.5.45
iTunes Serial Number 00C8AA740D118CA8
Current user is not an administrator.
The current local date and time is 2012-05-26 11:33:21.
iTunes is not running in safe mode.
WebKit accelerated compositing is enabled.
HDCP is supported.
Core Media is supported.
Video Display Information
Intel Corporation, Intel(R) HD Graphics
**** External Plug-ins Information ****
No external plug-ins installed.
iPodService 10.6.1.7 (x64) is currently running.
iTunesHelper 10.6.1.7 is currently running.
Apple Mobile Device service 3.3.0.0 is currently running.
**** Device Sync Tests ****
Sync tests completed successfully.

Unchecking and rechecking songs worked for some but not all songs. Recreating the library, http://support.apple.com/kb/HT1451 , works.

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Hey apples
When i sync my itunes playlist to my iphone 4, it syncs correctly, just to clarify that (at least, somewhat correct). However, since the IOS 5 update, my Iphone playlist is not showing all the music it's supposed to compared to the itunes playlist.
I have double checked my itunes library, and it's fine there, but once i enter the Ipod app (or music app as they call it now....) it doesnt show all the recent tracks i added to the library. Funny thing is, they were there before the IOS 5 update....
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PS: Using itunes 10.5 on windows 7 64 bit
Best Regards
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