We don't do as much travelling as we would like since we both retired but we sure do lots more than before.
We seldom do the exact routes, either. That's why I have accumulated so many motels and prefered gas stops in the three western-most provinces! But we do head west frequently and there are parts of any trip that are common, depending upon which mountain pass we plan to go through to get to British Columbia. And we do have a few favorite places we like to go, even though we try to find new ways to get there (eg. Regina, SK to Vancouver, BC via Dawson Creek, BC, Tumbler Ridge, Prince George, Lillooet, Pemberton, Whistler). I'm becoming notorious among family and friends for being able to compress a three-day trip into two weeks.
Most of my advance trip planning has little to do with maps and lots to do with "What is there to see and do between here and there?" Once I find something interesting, and we have decided some of the things we want to do, we'll look for interesting accomodations. It's not until we have reservations somewhere that I finally do anything related to maps and waypoints.
At that point I find the location of our motels and of any preferred gas stops along the route and plug them straight into the iQue. I use the iQue's "Find" capability so if I get a hit I can just save it as a waypoint and don't have to enter anything. The iQue just copies all relevant info from the POI database into its address book. Otherwise I find it with Google Maps, point to the location on the iQue's map and save the point as a waypoint. This, of course, requires me to manually enter all the other information. I generally end up manually entering perhaps a quarter of the waypoints.
Until I got my laptop this summer I did all the on-the-road planning with the iQue alone, and the CAA (Canadian version of AAA) Accomodations Guide. For some strange reason Garmin did not make it possible to transfer waypoints and routes from MapSource to the iQue so I'm still in the habit of doing that part directly on the iQue, even with the laptop available. Now that we have the laptop on the trip we just use MapSource like you would a paper map, the advantage being that you can zoom for detail and easily check the distances between two or three different potential routes to the same place.
As you mentioned, Streets has a much more attractive display for the maps, so we may use it more than MapSource for on-the-road planning. But Streets maps are Navteq-supplied data so I don't find any difference in the accuracy between Streets 2008 and Garmin City Navigator North America v8. All the same omissions and errors that I'm already familiar with in the Garmin product exist in Streets.
I find Streets horribly slow to load. On my desktop it takes 25-30 seconds to display the map on startup versus 4-5 seconds for MapSource. Both are slower to start on my laptop but still the same magnitude of difference. Not being a particularly patient person, if I want something quickly I'm still more likely to fire up MapSource .. or just grab my iQue. From turned off, push one button and it has the map up and ready to go in under two seconds. Even I can wait two seconds.
...ken...