Miranda, I feel I didn't give you a good enough answer earlier and I don't want the contrarians to confuse you. Keep in mind that I am a Roku User/Owner and prefer the Roku to the Apple Product. I believe you are looking for a simple solution, not complicated? It is really going to come down to how much you're willing to do to make it work. If you want it to work out of the box with Apple Itunes... buy the Apple box. If your willing to do some server setups, file conversions and a fair amount of tinkering, then go with the Roku... you can make just about anything work with enough effort. The Roku will never have a native Itunes application as it is a competing device that is partnered with Amazon's VOD service. Because of this, and limitations of the Roku supported file types, there will never be a direct way to play things you purchase off of Itunes. I hope this helps.
Yes it will. You need to download a software called Plex, it is available for both MAC and Windows. http://plexapp.com/. Once this is installed you can activate the PLEX channel on your Roku box. This will give access to all your iTunes video and audio.
no, Apple encoded movies are .mp4 or m4v files and they work wonderfully with the Roku BUT, and this is a big but, Apple adds DRM to movies purchased from iTunes so they only will work with Apple devices
Generally speaking, you can't play the iTunes movies using Roku because of the Fairplay DRM protection. But there are some third party software that can bypass the iTunes DRM protection losslessly, like the one I'm using currently: http://www.tuneskit.com/tuneskit-for-mac.html
Generally speaking, the Roku and Plex can't play iTunes movies, because the iTunes movies are encrypted by Fairplay DRM protection. So you have to find some 3rd party software to remove the iTunes DRM protection at first. As far as I know, TunesKit DRM Media Converter can do this. And I found a tutorial about your problem: http://tuneskit.com/drm-m4v-to-media-players/play-itunes-videos-with-roku3.html , hope it's helpful.
A cheaper way, if you have an ipod, is to transfer your videos to your ipod and then connect the ipod to the tv with a hdmi connector. Alternatively you could stream videos through your ipod to the tv via the air video app to save space on your ipod.