I just stumbled on this old thread as I was investigating a related problem. This problem annoys me greatly, Apple seems to be at war on list style views on all its devices and I suspect these problems will only become more widespread in the future, but for anyone still struggling I've found a fairly good workaround for now (currently itunes 12.5).
1: Whilst in itunes in the main "films" section, looking at your full list of movies in classic list view form, hit file>new>playlist (this is on Windows, maybe there's a slightly different menu on MacOS, but you know what I mean, you're creating a normal itunes playlist, just like you might for music. Maybe call it "films for ipad" or whatever you like.
2: drag and drop whatever movies you're gonna want to sync into this new playlist, just like you would making a music playlist.
3: Now with your ipad or iphone or whatever connected, go to the "films" section where you normally choose what you want to sync (with the horrible grid view that's causing the problem), ignore the big grid view, don't bother selecting from that. If you scroll down (the outer scrollbar at the edge of itunes window, not the one inside the films grid view), you'll see below the big grid view, a little box called "include films from playlists". So tick the playlist here that you just created in step 1, and all the stuff you put in there will be sync'd to your device in one go.
From now on, just maintain and update that playlist as you like, and it will always sync up to date each time you connect your device.
Hope this helps - at least until Apple mess up that functionality too.