Actually, I agree that the media organinaztion needs work. For example, I have 5 recordings of the same series in MythTV, just different episodes, LinuxMCE handles this by repeating the Series name 5 times... not cool... Also I have some a lot of permanently saved series recordings organized by Series/Season/Episode Number - Episode Name.Extension, because they are all tv shows they all show up with the rest of the Myth recordings and only display Episode Number - Episode Name... again not cool...
It's not just his certain setup that requires a change in how this is handled. Just about everyone with a lot of media has this problem... There are better ways of doing this, but it would most likely require database changes and Rolodex type of UI, kind of like MythTV has for its recordings. You wouldn't need too many changes, just the ability to have multiple levels of search. For example, lets say the UI looks just like it is now, only that one incantation of the Series name would be displayed, then upon selecting that Series name the menu you are currently working with gets pushed over to the left and a new one is created to the right that lists all the Episodes for that Series. This can be expanded to suit the needs of all.