Jumping in here, need to express an opinion based on lots of use:
Of the three major Windows travel planning packages out there, only one
seems to really do the job:  Microsoft Streets and Trips, right now
available at Costco for about $15 after rebate (new 2002 edition).
The other two packages (and I tested out current versions just three
months ago) run a far behind second and WAY back third place.  The AAA
Delorme Map and Go is OK except that it prefers to have the CD loaded
when running, but does a good job of route planning.  The Rand McNally
package is really, really poor compared.  I base most of this evaluation
on the ability of the packages to find a specific location or address.
I tested using known addresses and destinations I was going to on a
trip.  Rand McNally couldn't find ANY specific address I knew I was
going to, could only direct me to the general location.  If even a
little bit off the main roads, it was lost.  At that point I returned it
as totally inadequate.  AAA Map and Go works fairly well, and could have
done the job, but Streets and Trips has MUCH more details, especially
when you go off road (forest service roads, trails, etc), especially in
the new 2002 version (I upgraded about a month after this last trip). I
know that recommending anything from Redmond is like suggesting a Ford
Econoline would be a great conversion van for camping (not) but Streets
and Trips is by far the better of the three packages.  It doesn't seem
to have an expense record keeping feature, but I can live with that
given the tremendous flexibility in trip planning, and the fact that I
have yet to come up with a destination or waypoint that it can't find.