I'm looking for a better way to enter travel itinerary info into the
calendar of outlook.

More specifically, it drives me nuts that there isn't a way to enter a
roundtrip plane tkt trip as a single, coherent entry--ie, one entry
session that ends up with two calendar entries with start and end
dates/times corresponding to the takeoff and landing times of each
flight.  I am NOT interested in a separate application--entries must
end up in outlook (blackberry syncing going on, group scheduling, etc.
so I don't want another app with its own data set, no matter how nifty
that app may be).

SO one good answer might be an add-in that does this.

Another good answer might be a more general utility that would create
(or at least take a guess at) outlook entries from raw/semi-structured
text (I may just be dreaming here!--ie, I fantasize that there would
be a little utility that would accept text pasted from an itinerary
(or anything else really that contained dates and times) and this
little utility would recognize dates and times (not that hard) and
then guess at subject etc. and then propose an outlook entry.  (more
complicated but not that dissimilar to what google itself does when
you type an address in--it scans every query and if there is a zip OR
if there is a state preceeded by a recongizable town preceeded by
something that looks like an address or ... long ago lotus had a
lovely but short-lived app called 'agenda' that did this, it would
read a string of text and if it found days or months or relative day
terms ('today' 'tomorrow' 'next week' would then tag that entry with
the related structured data...

of course if all the travel services and airlines did what avis (and
opentable) have started doing (offering an outlook entry once one
makes the reservation) this whole question would be moot.  But since
they don't...