So I dug into the C:\Windows\Software Distribution folder and manually kicked off the 500MB+ beast. It very quickly came up a message indicating why the Windows Update attempts failed. Since this server was going to be accessing some iSCSI LUNs on a Dell Equallogic array, I had early on installed the Equallogic Host Integration Tool Kit (aka HIT Kit) to get the benefits of quick configuration of the initiator and the MultiPath IO plugin(DSM). The SP2 interactive installer clearly pointed out there might be a compatibility issue with the DSM driver along with an option to "Ignore and Continue" - which I selected. The SP2 installer went about its merry way, installed without issue and all SAN luns were fine afterwards. A plus in favor of Windows Update is that it plays its cards conservatively (in this case) - a minus was the hexadecimal cryptic error message it provided back.
Lessons learned - Do all your OS related patching before adding anything else to your system and run installers interactively when issues crop up. Share knowledge with others so that Google may more quickly end their similar tribulations ;) .


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