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The easiest way to view videos that are on your Mac or your PC on an iPad is an app called Air Video. You run this as a server on your desktop (very simple to do, no network skill set needed) and then the app on your iPad is your client. If your iPad and your desktop are on the same wifi network the iPad will automatically see and access your desktop. If you are off somewheres you can be in a hotspot and access your desktop's movies via the internet. The upcoming 3G iPads will, of course, be able to access the movies over the internet by 3G.
One of the most interesting things about this app is that it will seamlessly convert movies on the fly. So if your desktop's movies are all avi's (for example) you will not need to convert them to mpgs. Most surprisingly the process does not cause any video stuttering, unsynched audio or other problems. So, I have about 200 movies on my iPad!
Oh, one caveat -- if you bought movies with DRM it will not access those.
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