Is there a way to explore my WHS files via Xbox 360's Media Center app?

"I dont think you can install Windows Media Center on WHS, which you would need to do to be able to connect it to the 360.

But, you can use Media Center on your laptop and extend that to the 360. Then to access the data from your WHS just add the relevant folders from WHS in Media Center as shown in the picture.

Regards to the Video folder, I dont really understand why it has this behavior, so I cant help you here.

Hope that helps.

(...ctd from below) You could try Vuze (Yes, I know its also a bittorent client, but its the only program I am aware of that converts files so easily) which automatically converts videos so they are playable on multiple devices, incl the Xbox 360. Once you add them to Vuze, it will detect the device you want it to play on and start to convert them to a playable format. Once they are done, they are accessible on the Xbox for watching. This isnt ideal though as it means converting every video file that isnt comaptible, and it means not using Media Center which kinda defeats the object."