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I'm not new to web design, but I am new to putting videos on my site.
I want to keep my users on the site at all times (so I don't plan on using YouTube).
Where do I start?
At the time of writing Flash video (FLV) is the dominant format - you don't necessarily need Adobe's authoring software if you find the expense prohibitive as there are open source ways to create FLV files (e.g. ffmpeg) and numerous free or cheap "players" such as FlowPlayer (though in my view nothing is as good as Flash itself).
There are many other formats to choose from and things can change very fast, but Flash currently has the widest installation base amongst users and better cross-platform capabilities than most.
All of the above assumes you are not targeting handheld devices.