To play the videos in a loop, you'll probably be better off using wmv videos as you can set up a playlist using a .asx file, although there is probably a way to do it with quicktime files as well but I don't know how. I take it you know how to encode the videos to wmv already.
Basically to stream the videos you want various bit rates so people can choose what sort of quality and size they want. Streaming the actual video is easy, just add a media player object onto your website where you want the video to play, and set it to the relevant size, if you're using wnidows media player for the media player you need to add on 72px for the height of the player as this is where the controls go.
To stream all the videos in a loop you will need an asx file, which you can make in notepad, you can copy the code for my asx file, which is
<asx version="3">
<entry><ref href = "hqtitle.wmv"/></entry>
<entry><ref href = "hq_maxpayne.wmv"/></entry>
</asx>
My asx file is in the same folder as the videos so I can use the short files names, to add more videos to the playlist, just add extra
<entry><ref href = "file.wmv"/></entry> lines.
My .asx file is saved as stream.asx, you then set this as the file to play in your media player, so the media player code on your page will look something like
Code:
<embed
type="application/x-mplayer2"
pluginspage="http://www.microsoft.com/Windows/Downloads/Contents/MediaPlayer/"
width="640"
height="552"
src="stream.asx"
FileName="stream.asx"
autostart="1"
showcontrols="1"
showstatusbar="1"
showdisplay="0"
autorewind="0"
PlayCount="1"
ShowPositionControls="False"
EnablePositionControls="False"
EnableTracker="False"
></embed>
The code I've listed is for the high quality stream of this max payne video on my website
http://www.mia-media.co.uk/videopage/maxpayne.html so you can have a look through my source as it is on the actual page as well.
Hope that helps, let me know if you have any more questions.