Let's get some video going first. Android natively supports mp4 video files with the H.264 codec very well, but it's unlikely that all your video files are already in that format. No problem, you can convert them for free with Handbrake. When you run Handbrake, open the source file you intend to convert. Set the output directory and file name if you haven't already set that up. There are a number of presets available, one of which is iPhone/iPod Touch. That will give us the file output we need, so just pick that one. You can allow this to convert if you like. However, this defaults to the resolution of the iPhone (HVGA). If you have a phone with that same resolution, you can leave it as is. But users of phones like the Nexus One or Droid, should change the width to take advantage of that extra space. Check the Picture settings in the main window. Set the width to that of your device. Check "Keep Aspect Ratio" as well to avoid stretched video.
But there's still all that dragging and dropping to get the actual file onto your phone. iTunes provides an elegant syncing experience for Apple products, and there's a similar option for Android (and other phones) called doubleTwist. It will sync media to your phone much like iTunes does, it even bears a striking resemblance to Apple's software. With doubleTwist you can sync music, pictures, video, or even iTunes/Media Player playlists. The doubleTwist software can be downloaded here.
Simply run the install file, plug in your Android device, and put it in mass storage mode via the pull-down notification. There is a doubleTwist app in the Market that does this for you automatically, but it costs $.99 and it's really only saving you from one action. When connected, your device should appear on the lower left of the doubleTwist window. In the device interface you can select what sort of media you'd like to sync. The tabs at the top of the window allow you to pick which files of each type to transfer. When you're done, just hit "Sync " and doubleTwist will transfer the files.
Follow these steps and you'll have media on your phone in no time. Sure, you have to do a bit more running around to get everything set up, but once you do it is a surprisingly hassle-free experience. Hit us with any media management tips you have in the comments.