People have tried this before.
- http://www.nuim.ie/staff/dpringle/gis/lectures.shtml - good straightforward lecture notes. pdf & a little wordy but solid
- https://github.com/veltman/learninglunches/tree/master/maps - great 50% concept 50% practical guide
- http://pragprog.com/book/sdgis/gis-for-web-developers
- http://pragprog.com/book/gsdgis/desktop-gis
- http://toblerity.org/fiona/manual.html#introduction
- https://github.com/mikelmaron/Cartonama/blob/master/cartonama.md
- http://courses.ncsu.edu/mea582/common/GIS_anal_lecture/GIS_Anal_Lectall.html
- http://skagit.meas.ncsu.edu/~helena/
- http://www.qgis.org/en/docs/gentle_gis_introduction/index.html
- https://github.com/maboa/shape-journalism