It seems that the process is not that bad (even though your description does look a lot worse). Subscribe to the Microsoft Security Bulletins and they have a full description of each patch that they put out on Patch Tuesday (e.g., https://technet.microsoft.com/...). The same goes with RHSA. Subscribe to the updates that you are interested in; these will most likely be your OS, web servers, app servers, other software installed. Similarly, most vendors run security patch announcements. There will likely be a lot of noise but in a couple of months you will know how to extract the information the change advisory board needs. Here's the positive aspect of CAB: if you screw something up, you have someone else to blame! ;-)

By the time they fix the clock, it'd be 100 days and the clock would be slower by 100 days! Then they'll try to fix again and the clock would be slower by 100 days again! ....ad infinitum... Better to break that cycle by not embarking on this journey!

Read Avinash Dixit's Thinking Strategically to get started. It's a great book which does not use much math and can make for light reading and a great start.

If they use some kind of domain administrator passwords for this software to run guess what, the domain administrator credentials could be cached in every single computer. If a local administrator was on the machine and wanted to compromise, he/she could run hash stealing software when this "process" runs and compromise the domain. The least possible privileges for a process that does this data searching will be difficult to determine. A trade-off will have to be done between accessibility of files and a lesser privileged account to be used for an exercise like this on Windows.

http://carnal0wnage.blogspot.com/2010/03/fking-with-foursquare-goes-msf-style.html

The credit card companies and banks are wanting to shift the residual risk to the customers. That's why they want you to pay for "SafeProtect" etc. for which you have to pay in advance so they monitor any ID thefts. My question is shouldn't they already be doing that? If yes, then why do they want you to pay for it? Cost reduction in my humble opinion.

I have some dd images (raw images) of some of my old computers that are about 350 GB large. Of course, the largest /dev/sda on my PCs is 320GB big.

Better than being called Dilbert.

I think apple should launch another ad campaign with the "Cool" mac guy on one side and a security guy on the other! The "Cool" guy could put his head in the sand and shout "Don't make me do stuff!".

Well...he got the money from a by-product of a fringe benefit of the hack (Hack->useful information (insider info)->steal). Would a similar argument be applicable if he was able to siphon money from individuals' accounts had he gained some passwords (Hack ->useful information(passez) -> steal). I wouldn't think so.
Agreed, that he was not an insider so he can't be convicted for insider trading...but there should have been at least one more lawsuit going against him!