Weird, I could have sworn I posted a response, but it looks like it didn't go through...
Anyway, I worked mostly with Pepperwhite street (Don't even think it's around anymore), Arcview, MapObjects and LeadTools.
Pepperwhite street for the presentation aspects (they could get the entire US streetmap into 550mb, which in 2000 or so was a pretty good trick), Arcview for gis data manipulation and cleanup, and leadtools to layer images (large scanned fema flood zone map images) over the digital maps for annotation and georeferencing.
Haven't had much exposure to the latest web mapping stuff (other than to play with the Google Maps Layers), but I'd love to have reason to
