We do not have a VPN which means we can't watch anything online at like ABC, CBS, NBC, or what not. But we have had no issues with iTunes. I have issues getting on Disney.com and stuff. And Yahoo turns Korean once a week no matter how many times I set it to english. 4Shared, and Bing are always Korean no matter what. I've learned to deal with most sights and no which buttons to click to get what I need/want to download.
Our AFN picks which shows they want to air and usually only pick 1/4 of what is on in the states. Then like 6 months later they may chose an old show that was on in the fall or what not. Its crazy! To me its not worth all the hassle. iTunes has a pause button. If you turn off the tv or hit the menu button it remembers where you left off so you can pick right back up.
We have Korean internet which is dirty cheap and unlimited. Even like with the phone plans, 3G is dirty cheap and its free to tether. I will miss that. But the speed varies a lot based off the time and people. Holidays/weekends are impossible to do a lot online. Dling or upload will take days if you start on the weekend. But I try to remind myself that we only pay like 20,000 won a month for internet. Roughly like $18 in dollar. It is our only option too as there are not options for things like this in Korea, there is the one choice and that is it.
I guess I went on and on with more than just your questions, sorry. But I have to say I adore iTunes living overseas. It has made my life here a little better.
(oh and before coming to SK I was anti Apple, but I have come more towards the light)