Why is ical 5.0.3 search inaccurate?

For example, if I type in "Dad" then I get Dad events but a number of other events without the word dad.

Apple does not comment on their design decisions, and certainly won't do so here. If you want to comment to Apple, you can do so via their feedback page:
http://www.apple.com/feedback/macosx.html
The only way to "resolve" the issue as of right now is to use some other calendar application. But even BusyCal, the most common iCal alternative, doesn't display more than one month at a time in the sidebar.
Regards.

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