Digital Charts
After looking around a bit, I'm pretty happy about the current state of electronic charting. First, NOAA has made available both raster and vector charts for free. The raster charts are in BSB format. Vector charts are in the ENC format. So far there only appear to be two drawbacks to them here in the Bay Area. Drawback number one is general and that is there isn't yet a really good way to check for updates to either automatically. That feature is one of the most promising as these charts will receive updates from the weekly Local Notice to Mariners. The other minor issue is that there are a couple of gaps in the vector/ENC/S57 charts in the Delta. Oddly the region between the Benicia bridge and Pittsburg is missing. The central/west Delta is well charted from Antioch to Tinsley Island. Also note that the Sacramento River is missing much vector charting as well. The raster charts don't suffer any of these problems.
One huge new benefit is to be able to get raster and vector charts for most all around North America.
I also looked at chart plotting software. As a current owner of Nobeltec VNS, I was pleased to learn that Nobeltec 8 supports both types of charts. Passport Vector charts are superior due to Nobeltec's implementation. I tried a bunch of the other charting software options and the only other one I can recommend is Rosepoint's Coastal Explorer. I had to stay with Nobeltec (I needed to upgrade from 7) as the Delta vector charts are important to me, I'll need to wait for NOAA to make those available before I switch