ITunes can't connect to store

I recently moved all my files (using Migration Assistant) from one computer to another. I then sold the first computer after erasing all data from it. My iTunes data didn't migrate for some reason. iTunes just opened as a new, empty app. on the new computer.   But, fortunately I had all the audio files backed up on an ext. HD. So I just dragged and dropped them on the new iTunes.    Every thing is appearing and playing fine, except any songs previously purchased from the iTunes store. They present a message saying "this computer is not authorized to play—title of the song—" and inviting me to fill in my Apple ID password and authorize it.
When I fill in the requested info and try to authorize it a prompt tells me iTunes cannot connect to the store and I should check my internet connection.   My internet connection is fine.
When I tried (as suggested by one of the iTunes support articles) to deauthorize then authorize the computer, same "check my internet connection" prompt.
I tried to update to the latest version of iTunes (I'm currently running iTunes 4, don't know what I was running on my previous computer) which I downloaded.   it tells me it only runs on Mac OS 10.5.
So ho I have to upgrade my iTunes software and my Mac OS in order to solve this problem? Is my Mac OS (10.4.11) the reason why my iTunes won't connect to the store?
Any suggestions would be greatly appreciated.
Thanks,
John

When you reach 5 authorizations, you can deauthorize all and then authorize only the computers you have.
Authorization FAQ: http://www.apple.com/support/itunes/store/authorization/
About iTunes Store Authorization and Deauthorization: http://support.apple.com/kb/HT1420

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toonz,
this is the file from the network diagnostic I did while still running 7.4.2.4 - I also sent it with an email to the tech support for itunes store; so far all I've heard back is that they are working on it and will send me an email when it's fixed. (by the way, I deleted the ip addresses etc. but everything else is the same as it was then.)
Running itunes 7.3.2.6 is working fine, by the way, I was immediately able to connect to the store and download. If anyone else is thinking about downgrading, try saving your playlists first (search for 'saving playlists' in itunes help) because you won't be able to use your old itunes library file. I don't know if saving the playlists separately will help, since I didn't know that would happen when I started. meeshala
Microsoft Windows XP Professional Service Pack 2 (Build 2600)
Dell Computer Corporation Dimension 2400
iTunes 7.4.2.4
Current user is an administrator.
Network Adapter Information
Adapter Name: {6F864B09-4D02-4FEC-989B-B1AF189789CC}
Description: Realtek RTL8185 54M Wireless LAN Network Adapter - Packet Scheduler Miniport
IP Address: [deleted]
Subnet Mask: [deleted]
Default Gateway: [deleted]
DHCP Enabled: Yes
DHCP Server: [deleted]
Lease Obtained: Tue Sep 18 15:45:29 2007
Lease Expires: Wed Sep 19 15:45:29 2007
DNS Servers: [deleted]
[deleted]
Network Connection Information
Active Connection: LAN Connection
Connected: Yes
Online: Yes
Using Modem: No
Using LAN: Yes
Using Proxy: No
Firewall Information
Windows Firewall is off.
Connection attempt to Apple web site was successful.
Connection attempt to iTunes Store was successful.
Secure connection attempt to iTunes Store was successful.

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