I removed the checkbox to create an ISO, and got a bit further... I could create a local HTTP server to pull the file from, but I'm wondering if I just end up in an endless loop of adding more and more files to make this work.
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Starting WSUS Offline Update download (v. 6.6.5) for w2k enu...
Cleaning up existing directories...
Downloading Sysinternals' NTFS alternate data stream handling tool...
--2012-12-10 15:07:11-- http://download.sysinternals.com/Files/Streams.zip
Resolving download.sysinternals.com... 213.199.148.241, 213.199.148.163
Connecting to download.sysinternals.com|213.199.148.241|:80... connected.
HTTP request sent, awaiting response... 400 Bad Request
2012-12-10 15:08:28 ERROR 400: Bad Request.
ERROR: Download failure for w2k enu.
Press any key to continue . . .