Problem after downgrading back to ITv.6....missing music during iPod synch?

Question

I recently happily downgraded back to iTunes v.6 after experiencing a nightmare with iTunes v.7. Since re-installing v.6, everything is fine except for one strange and annoying problem. I'm hoping someone can help, so here goes....
Now, when I synch/update my iPod as I had always done (not automatically, but with selective playlists checked), about 400 of 1700 songs do not transfer from my G4 to the iPod. However, when I switch to update with the automatic option to include all playlists, all 1700 songs transfer over to the iPod. I believe I've narrowed this problem down to one particular playlist which may not be getting recognized by the iTunes library. In other words, I want this one playlist to appear in iTunes, but not on my iPod. But, if I try to update with this one playlist unchecked, 400 songs do not transfer over. This seems odd since all music files (mp3s) from all playlists are located in the iTunes music folder on my hard drive.
So, my question is....how can I go back to updating my iPod to include all of the 1700 songs in my library, but without the one particular playlist (which is quite large)? As was the case before the iTunes v.7 debacle, is there a simple way to get my library to recognize the particular playlist so I can update my iPod selectively without putting that playlist on my iPod? I've tried to do some online research before bothering the wise people on this Board and it would seem that I either need to: 1) somehow import that particular playlist back into my iTunes library or 2) create a new iPod library file which I understand may cause me to lose my playlists and comments. I'm afraid to do either without some guidance, for fear of making the situation worse. I'm not very technical and I'm guessing there's a simple fix for this, so I'd sincerely appreciate any help and advice. Thanks very much.

Answer 1

Here's the log:
Process:    
Safari [23855]
Path:       
/Applications/Safari.app/Contents/MacOS/Safari
Identifier: 
com.apple.Safari
Version:    
Build Info: 
WebBrowser-75345910~1
Code Type:  
X86 (Native)
Parent Process:  launchd [278]
Date/Time:  
2014-05-07 16:14:33.635 +0300
OS Version: 
Mac OS X 10.6.8 (10K549)
Report Version:  6
Interval Since Last Report:     
235635 sec
Crashes Since Last Report:      
22383
Per-App Crashes Since Last Report:   13
Anonymous UUID:                 
6AD6BC48-95D3-42C3-A22F-66FAE28F420B
Exception Type:  EXC_BREAKPOINT (SIGTRAP)
Exception Codes: 0x0000000000000002, 0x0000000000000000
Crashed Thread:  0
Dyld Error Message:
  Library not loaded: /usr/lib/libc++.1.dylib
  Referenced from: /System/Library/PrivateFrameworks/WebKit2.framework/Versions/A/WebKit2
  Reason: image not found
Binary Images:
0x8fe00000 - 0x8fe4163b  dyld 132.1 (???) <4CDE4F04-0DD6-224E-ACE5-3C06E169A801> /usr/lib/dyld