Should I reinstall my current OS - 10.4.11 or upgrade to next version?

Our family of apple itouch, iphone, etc. users is having difficulty connecting to itunes, and uploading our photos to websites. I'm thinking that itunes and these sites have advanced beyond my current OS. Apple Tech suggested I reload my OS first and then if that did not work to upgrade. What are the steps involved, and has anyone else had similar issue to resolve?

Assuming you're having issues with the iMac noted in your profile, trying another network connection wouldn't an easy troubleshooting step. However, if the iMac is currently connected to your network via a wireless connection, please try using a wired (Ethernet) connection if possible.
Have you tried more than one user account on the computer?
What type of internet connection do you have?
Also, if you could go to this site: http://pingtest.net/ , perform the test & report back with the numbers for *Packet Loss*, Ping and Jitter. That website will give information about the quality of your internet connection.
~Lyssa

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