jtardie
http://mapbox.com/ http://leaflet.cloudmade.com/
Both have been gaining quite a bit of traction lately. Certainly worth checking out I think.
Regarding comprehension, maps seem to be efficient. Not sure of any ways that intuitively make as much sense as a well made map.
Did my best to pull out the good parts on github if anyone's interested...
https://github.com/jacquestardie/text-notes/blob/master/Crea...
In short, I'm happy I chose a job. Granted, I was lucky to get one that is doing work I consider meaningful. But having that job has made it much more clear to me what I'd like to do in the future. The MS I'd apply to now is dramatically different than the one I'd have applied to before having the experience. Which is a good thing I think.
Aside from that, I'd love to be further ahead with geospatial python and statistics than where I am now.
Mises.org is a good place to start in that regard.
Maybe a little different than what you were asking for but I think you'll like it.