I'm a new/first time iPad owner. I have had my iPad for just over 2 weeks.
Among other apps I planned on using, I want to use my iPad to play music video's. Like iTunes, but with music video's, vs mp3 files. I have about 1400 videos, but that number is slowly growing.
On my Mac, I would have used either MPlayer or VLC. As far as I can tell, MPlayer does exist yet on the iPad, and although VLC does, it doesn't have all the features I require yet. As such, I have been looking at a lot of different media players on the App store. I have also wasted a bunch of money there in my exploration.
Anyway, to bring this back into topic, the one thing all these players had in common was the upload/download capability sucked, and especially for large quantity of files. Yea, the drag and drop thing is there, and I haven't found it to work good for any of them.
Anyway, I ultimately just jailbroke my iPad. It works great! Not that I ever doubted Apple, but under the GUI, there is Mac OS X Unix.
I made a common place to store all my files, so I am not having to keep uploading video's to my iPad everytime I decide to buy a new media player. I just make a symlink to the new applications "Documents" directory, and I am good to go.
And when I add/remove/modify files on my desktop, I just rsync my video directory to my iPad, and I am good to go.
Ease of use, the ultimate in flexability and capability, and best of all, no evil cloud to contend with.
And this works just as well with photo's and movies I make using my iPad.