I'm actively involved in Geocaching and am always on the lookout for mapping software. Here's what I use and my opinions of what's on the market (and what I've tried)
Microsft Streets & Trips 2002.
A good solid release from Microsoft. Of course, like all past and current releases, S&T's maps fall out of date quickly. There is no update functionality built into the system except for road construction. The 2005 version was out of date upon release and even MS admited to this. Reviews of the 2005 on Amazon are low and mixed. But for me, the 2002 version is great. The GPS feed is limited but the ability to set differenet speeds on different types of roads is a plus. For example, I'm taking a month off this summer to travel through Colorado, Wyoming and the Dakotas. I set S&T to keep me off highways and only use 2 lane byways to see the real america (National Scenic Byways). It was a steal at $19.00 when I bought it three years ago and I still use it today.
DeLorme Street Atlas 2005
I bit torrented this one last week and tried it this weekend during a geocache in the Santa Cruz mountains. The GPS Feed was excellent; not only speed, heading, position but also satellite status was exchanged between the GPS and the software. This way, I didn't have to look at my GPS Screen to check signal strength. The GPS data was also displayed much larger than in S&T making it easier to see in the car. After using S&T for 5 years, it'll take a little bit of time to get used to the interface and my hacked copy is missing some of the search functionality (ISO error). But otherwise this seems to be a good buy. The built in voice prompt driving directions tool seems nice, though I don't use it. Nice color and interface.
Magellan Road Atlas and Topo Maps
I use a Magellan Sport Trak Map GPS, so I thought I would try out their software (bit torrent again). And boy does it blow. GPS data is uploaded or download and I don't see anyway to do live feeds from my receiver. The maps are ugly. Yucky. Only redeeming quality it the ability to upload topo maps to my receiver... very important in mountain hikes. (and topos don't change year to year except for the mud slides in California)
EasyGPS
Totally free waypoint and route database managment software. I download waypoints off the net for my caches and use EasyGPS to handle the uploads to my receiver. A great free tool.
Overall:
My biggest complaint so far is the lack of updates. Like paper maps, you have to buy a whole new atlas every year to stay current even though the technology is out there to update you electronically. But honestly, where's the money in that?
Anyone use any other mapping software or have experience with any of these products?
Also, has anyone out there used WWMX's (World Wide Media Exchange) travelouge? It's a neat tool that tags photos with GPS data allowing you to build a map of your route with clickable images based on GPS coordinates and dates. It would be great to build a travelogue of my summer trip. Something like this: