My daughter has two young children who watch videos when they ride and I wanted to share my experience through my daughter with the video USB connection.
One problem with very small children is that they can't control it themselves - you have to reach back and touch the screen and call up whatever settings you need. (I have found the remote to leave much to be desired).
But after connecting my iPad via the USB video port, I could only play music - it would not display movies that I had on the iPad via iTunes and Amazon Prime player app. After I could not get an iPad to play video through the video USB connection, I called UConnect care. The guy only had the user's guide and was little help. But I received a follow-up call from Chrysler. He explained that the video system will only play .aac and .mp4 files through the USB connection.
As I expect most people do, we play iPad videos through iTunes downloads or through our Amazon Prime app. So these video formats will not play on the Chrysler system - according to the call from Chrysler headquarters. If you're expecting to plug in your USB connection to your mobile device (phone or tablet) and play files from your iTunes video or Amazon Prime (or perhaps other services) they will not work.
There are two basic work-arounds. The first is to use the HDMI port and get a connector cable. For iPad there is a lighting port video hub you can get that has an HDMI female port. You can then get a short HDMI cable and connect directly to the Chrysler screen and use it as a mirrored display. The cons to this approach is that you can't use a single iPad to run a movie on both screens, and because it basically uses the screen like a TV, you can't control the volume with the device, you have to reach back and use the touch screen.
The other workaround is to convert the video files into the useable .aac or .mp4 format. This requires a computer, as you can't do it directly on the device . . . though there could be applications that I didn't see in my research. But using this method: How to Convert Purchased Amazon WMV Video to AVI/MP4
I haven't tried this and it is a fairly labor intensive workaround. I can't say whether it works but I don't see why it wouldn't.
I'm quite disappointed, I have to say. After all of the hype about the entertainment system, and multiple media alternatives, I fully expected to plug-and-play with my iPad using iTunes video or Amazon Prime. This is 2016, right? I just wonder how much development they actually did with real consumers in mind? These days, it's all about mobile (I figure the DVD player is just to allow people to still use their old media but few are buying new DVD these days) and I can't believe that they would market a USB connection that wouldn't natively play from the most common video sources (e.g. iTunes and Amazon).
But I just wanted to pass along this info. Perhaps others have had different experiences.