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Stumbled across partial solution:
If I run PP 1.5 on the actual Windows 2003 Server and attempt the Check In it worked. Previously I was running PP 1.5 on an XP Pro Client only. Still something not quite right.
i dont remember PRP very well, but if you switch on logging level 8, and check the console.log and perhaps the server.log on the PRP server you may get some insight