I wanted to teach my son how to use a compass, something I learned back in my pre-GPS Boy Scout days. I started digging on USGS topographical maps. They finished with the basic mapping project in 1992 and are now in update mode. Their website doesn't give a lot of detail, but they said they will update the maps that have the greatest interest. Most of the maps around San Diego were updated in 1997 (except for the Encinitas one which was updated in 1975 making it fairly useless).
The USGS does offer free scans of the maps. Here is a good blog post on how to download the PDF's of the maps. I tried to print them out on regular paper but Adobe couldn't tile the larger image onto 8.5x11 paper, it just printed a scaled image or a single tile. The only way I could use regular sized paper was to select the area of the map I wanted and print only that selection (note that Foxit Reader does not offer this feature). It was trial and error to get the selection to fit onto one page, otherwise it would be cropped. I actually taped a couple pages together to get a usable map this way.
I still might buy software which I assume solves all these problems, but I would really like to find out if they update their maps more than the USGS or just use the same ones.