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Strongbox could interface with a Windows box that does the live show if you end
up using a Linux box for the rest of the site so that you can use standard tools.
Logins would generally go through the Linux box, which would run Strongbox,
then Strongbox could pass authentication tokens to the Windows box similar to
the handoff and plugin functionality in Strongbox.
Alternatively, over the last eight years exactly two people have used Strongbox
on Windows, albeit without the proxy check feature. Both were using Apache.
It's a major PITA, so the normal $100 fee wouldn't quite cover it and since I haven't
had any Windows boxes to use as a remote terminal for several years, we'd need to
have a qualified Windows admin available to handle some of the Windows stuff in
consultation with myself.
Given the amount of software and techniques used for professional sites that aren't
designed to run on consumer desktop systems, his best bet long term may well be
to find a way to do the live show through a network operating system like Linux, Unix,
FreeBSD, etc. Several webmasters have told me that they used Windows just to do
streaming video, either live or recorded. They weren't aware that Apple'sDarwin Streaming
Server is in many ways superior to Microsoft's streaming solution and runs fine on
Linux as well as of course on OS X, which is BSD based.
Another option which may well give him the best of both worlds could be to use the
Windows box just as an origin server feeding a network OS box (Linux, etc.) that would
actually send the feed to users. Just as you can use a Windows desktop to upload a
web page to your Linux server, I believe you can also use a Windows box to upload a
live video stream to a Linux server. Don't ask _me_ for the exact details on that, though,
my knowledge in that area is limited. I installed the Darwin Streaming Server once,
and read the documentation about it's authentication systems, but never understood much
about how it's used. There are plenty of people knowledgeable about Darwin and othwer solutions, though.
I'd ask some of the knowledgeable web hosts like Mike at Phatservers, Chris at ATCIhosting,
Sagi at Webair, or Luke at Chilihost for a referral, then hit the Darwin forums.