Windows Vista Parental Controls Preventing Connection to iTunes Store?

Question

I really have two questions, one of which I think I have resolved but would like to find a more elegant way of handling. Let's tackle that first, after I provide some background.
I have been "managing" the contents of my son's iPod using my computer. Now that he has his own computer it should be up to him. I have two users established on his computer, with me as administrator. I have set up parental controls and am specifiying the websites he can access. I used an external hard drive to copy all his music files to his computer, putting them in a folder under his user name.
When he tries to play music copied from CD's or purchased from iTunes using my computer, a message pops up that says "The song <song name> could not be used because the original file could not be found. Would you like to locate it?" Absent a way to locate all such songs simultaneously, I click on the yes button and scroll through the list of songs until I find the one desired. Is there a better way, or are he and I going to have do repeat this hundreds of times? I think this needs to be resolved before he tries to sync his iPod with his computer. Correct?
The second problem crops up when he tries to purchase songs from iTunes. The error message reads "We could not complete your iTunes Store request. An unknown error occured (-9808). There was an error in the iTunes Store. Please try again later." Apple.com is one of the sites he is allowed to visit, and there is no mention of parental controls or filtering (normally when that happens I am allowed to override with my password). Also, the computer has been authorized. Has anyone experienced anything like this or know what the workaround is? Does it have to do with parental controls, or is it something else?
Thanks in advance for your help.

Answer 1

Hello, Welcome to Apple Discussions.
I have a few things to offer that may make things a bit easier. You mention the library or music content is on an External HD and you copied it to his PC. Is the Hard Data aka the songs themselves still on the computer in a folder?
If so. Delete the songs in iTunes, Select 1 song, then Edit Select All, and Delete from Library. Now go to iTunes - Edit - Preferences- Advanced Tab
-Put a check mark in Keep iTunes Music Folder Organized, Copy files to iTunes Music Folder when adding to the library. Thus whenever songs get added into iTunes a hard copy will be copied into the iTunes music directory stored in
Music - iTunes - iTunes Music.
-Now exit out of Preferences, Go to File - Add Folder to Library - (assuming all the songs from the HD are in 1 massive folder) and browse for this folder. iTunes will scan it, add it into iTunes, and then copy a hard digital copy into the Music-iTunes-iTunes Music folder. You can go confirm the files are there by visiting the folder. The file size of the iTunes folder should grow as you add more and more music.
Back up your iTunes library by copying to an external hard drive
http://support.apple.com/kb/HT1751