PLEASE HELP! issues with syncing

o-kay. i am actually on vacation right now, but my ipod is a huge part of my travels and i'm having some problems.
i purchased a 30GB ipod video off of ebay and saved quite a few bucks in march. i haven't had any problems with it so far. it has worked like a dream!however, over the past few days it has been crashing and freezing up. so far, i have been able to restore it, and reset it so it doesnt freeze, but i can't get it to sync all my music from my itunes library. this is causing me stress.
any suggestions as to what the problem is or how i can fix it?
ibook g3   Mac OS X (10.4.8)  

FIRST click on “reset settings” (if it is grayed out and does not allow you to reset; just go to next step) Click on Configure settings; check off calendar; as soon as you check it the next screen just pops up It says select a device application; then scroll and select Microsoft Outlook; Click Next and then pick which way you are going to sync If it is the first time just use One way sync from outlook to device. Click next; Click transfer only future items selected; click next then finish; Should see the final screen with top box out of three checked off. Click ok Click sync at bottom right of page. I found that if I went to slow (since I was making this sheet) that I would get the error message sometimes. I would just start over; FIRST ALWAYS RESET SETTINGS; then just follow all the steps again . Then should sync Once it is finished you will be back where you started from It is a good idea to click on Reset settings now before you close out. When you go in again click follow the steps from the top of the page. FIRST click on “reset settings” (if it is grayed out and does not allow you to reset; just go to next step) Click on Configure settings;

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