I've played with most of the trip planning applications.
The online stuff I've tried are very short on options and features.
Delorme, which came with my GPS receiver for the laptop, sucks, period.
Microsoft Streets and Trips, in my experience, is by far the most flexible,
has the most detailed maps, and the most info on campgrounds, etc.  It's GPS
interface is not as good a Delorme but works.
And if others out there have found better software for planning a trip (not
for GPS tracking) I'd really like to know about it.  I'm sure something out
there is ideal, just haven't found it yet.
BTW, MS S&T has a learning curve like anything else.  But once you get used
to it it's great for planning.  Then the trick is to be able to follow the
plan.  In the real world that doesn't happen very often.  And I add at least
20% to the time estimates the S&T gives me.