The information stored on the system will determine how aggressive and how often the system will be attacked. Financial and personal information that can be used to commit fraud is highly sought after by crackers who can sell the information or make use of it for their own gain.
Another consideration is the popularity of the organization. Microsoft is despised by many as being a greedy, corporate giant that destroys competitors in an attempt to create something close to a monopoly. This reputation has caused the cracker community to attack Microsoft systems regularly, exposing the flaws in the software and turning many towards other, safer alternatives. This has cost the organization product sales revenue, as well as large amounts of money invested in security updates and patches developed and released to fix the weaknesses.
When working with a company manager in the analysis and design of an information system, often times it is all about the profit, or the "bottom line". It may be difficult at times to see a return on the investment into security, but the results of inadequate security can be disastrous and cost much more than the initial investment into adequate security.
I agree on need for security. It is over looked.
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