I strongly agree.  This a serious short-coming in Outlook and a big
opportunity for competing scheduling software.  I know lots of people
that struggle with this issue.
Microsoft's website
(http://office.microsoft.com/en-us/assistance/HP010223091033.aspx)
says:

Three factors affect the scheduling of a meeting in Microsoft Outlook:

The clock setting (time) of the computer.
The local time zone setting of the computer.
The daylight saving time adjustment setting of the computer.
All three factors must be set correctly on both the meeting organizer's
computer and on each attendee's computer to ensure meetings display at
the correct times.

*When you have all-day events on your Calendar and then change the time
zone, the all-day events span two days instead of one.

Outlook treats anniversaries, holidays, and birthdays as all-day events
(an all-day event is defined from midnight to midnight in the local
time zone). When the time zones change, all-day events move. Therefore,
when you change the computer's time zone, the all-day event moves to
display in the new time zone. An event, such as a holiday or birthday,
will appear in the Calendar on two consecutive days. For example, a
birthday could appear from 6 A.M. one day to 6 A.M. the next day.

You can do one of the following:

Use the additional time zone feature in Outlook to display the local
time zone and do not change the operating system time zone.
Correct each all-day event for the current time zone setting.
Change the time zone back to the one used when the items were created.

*You need appointments to be at fixed times no matter what time zone
you are in.

You want an appointment to show on the Calendar at a fixed time no
matter what the time zone is. For example, you want to be reminded to
take your medication at the same absolute time regardless of the time
zone you are in. However, when you change time zones, the appointment
changes to reflect the new time zone.

Outlook can't force an appointment to remain fixed when the time zone
changes. If you need the appointment to stay at a fixed time, you
should not change your current time zone. You can add the additional
time zone to track the other time zone times. To change the time zone
setting in Outlook without changing the times for each of your
appointments, you must export the data from your Calendar folder,
change the time zone setting, and then import the data into Outlook.

*You are traveling through two or more time zones and need to display
the local time for each appointment in Calendar.

If you are a salesperson in New York City, New York who has a breakfast
meeting at 8:00 A.M., then flies to Chicago, Illinois for a 1:00 P.M.
meeting, and then flies to Las Vegas, Nevada and has a dinner
reservation at 6:00 P.M., Outlook displays all of these appointments
relative to the time zone you were in when you entered the appointments
in Calendar. Therefore, in New York City when you look at the Calendar,
breakfast is at 8:00 A.M., the Chicago meeting is at 1:00 P.M., and the
Las Vegas dinner is at 6:00 P.M. However, when you look at the Calendar
in Chicago, the breakfast is at 9:00 A.M., the local (Chicago) meeting
is at 2:00 P.M., and the dinner is at 7:00 P.M.

The user should not change their original time zone and should use the
additional time zone feature to display the local time. You can only
display one additional time zone, so you may need to change the second
time zone each time you change time zones.