A  maojority of my library can nor be found?

I have over 500 songs on in my itunes libray and have been successfully downloading, creating playlists, and then downloading them to my ipod for 8-10 months now.
The only computer I use for itunes and the music store is my business laptop. When I travel I have been able to hook up to the inernet and download,play, update ipod with no problems
This past week I was on business and downloaded some musice while in the hotel room then went down to a conference room to play some of them at a breakfast and suddenly a message appeared asking for my username and password??? I tried and tried and despite loging in corectly could never get the music both new and old to play.
So i got home and back to the office and the same thing! It is only recognizing like 20% of my entire library? When I try to click on a certian song and it says "this song can not be found? And once again asks me to re input my username and password etc and once again NO MUSIC
My ipod even messed up in this process. Now my ipod lost songs as well. Let say I had 50 songs in a Jazz folder. Well now there are only 2? When I look at that same jazz folder in my lbrary on my laptop when in itunes I will see all 50 songs but when I try and play one of them the message comes up?
So I can't figure it out? Thoughts I am having...
When I allow my office mates to share my music at work (but not giving them my password) could his mess uo the whole "5 machine max can be authorized thing?"
Also I almost never even burn a CD from my library so the concept that I have used all this music "too many times" and now it i dead is urealistic I think??
I am thinking it has to do with eitehr synconization of my laptop tp my work newtrok? Or maybe my ituens music folder is not connetcing to my library somhow?? Last but not least i did do an itunes update about 30 days abgo so maybe late dec eraly January that seemed to download onto my ipod fine
Please help! I am dyin without all these tunes I have workes so hard to compile
Compaq nc6230   Windows XP  

Thanks! Tried this all this morning. Now what it looks like is that when i first started my itunes account i started it using my home computer and home email address. I downloaded abou 20 songs on that account/email address/computer. Right there after I got my busienss laptop and decided to not use the home account any longer and start a new one knowing that I would be using my laptop as my primary account. So, I started a new account, new credit card, new email, new computer. Moving forward I used this account for 500 plus songs with no probelm.
Well now when I click on a song the user name and passswrod pops up but already laid in there is my home emial address? The old account?? it is almost like itunes thinks that all this music was purchased on my old account? But it was not! i am sure of that. So even when I put in my old pass word it still does not play the music.
Oh yeah and when i went to my current account info meaning my business account with busienss email that i have downloaded all this music on it is saying I only have 1 computer authorized ???
Total confusion! Any other ideas

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