Actually, I am now emcountering a similar issue to yours
I can get the iTunes movies onto the SanDisk drive, but when I try to download them to the iPad, it won't download to the Videos app, but to the my Camera Roll where it doesn't want to seem to play.
I have a bunch of DVDs I converted myself and these will stream from the SanDisk drive right from inside the SanDisk App, but none of my purchased iTunes content wants to cooperate.
SanDisk just updated their app, again, so I wonder if this is the issue or it's Apple, again, putting limits on how movie/tv content will be handled on Mobile devices.
This ***** now for both of us. You are probably just going to have to sync up to iTunes and put those movies on your iPad if I can't find a resolution to this.
I haven' t used the newest SanDisk app with this drive in the last two months, but I had no issues getting purchased iTunes content on and off my iPad.
SanDisk changed something to now prevent iTunes content to even be downloaded back to the proper location on the iPad so it can be played properly from the iPad.
I am soooo peaved that this is no longer working, I can tell you!
P.O.ed!
This has got be Apple again, and/or SanDisk that created this new mess!
I feel your frustration.
This is a brand new issues and now I see why you have been having issues.
This previously wasn't a big issue/problem.
Somebody, once again, changed something was working to now preventing this from working!
Maaaaaan!
Sorry, but I didn't realise the extent of this issue.
I now know.
Trying to ascertain whether there is another workaround for this issue, now!
Sorry.