RE: GPS Mapping software
Hmm...thats a tough one. I don't have experience with anything other than the Garmin TOPO software, so I can't give comparative advice, but I can tell you I am thoroughly impressed with Garmin's product and it should be able to do everything that you want it to.
Once you download the maps onto you GPS, you won't have to do it again unless you want to change the areas over topo coverage. You can just update the points, routes, etc without changing the maps.
Hope this helps