Inspiration to model an Isaac Orloff illustration taken from another CG Cookie user who expertly modelled his own illustration.
https://cgcookie.com/blender/images/isaac-orloff-illustration/
http://theconceptartblog.com/2011/09/18/home-sweet-home-a-arte-de-isaac-orloff/
Still a work in progress. I have tried to stay true to the illustrative style of the original.
I tried to use displacement for the wooden planks (only on the main part of the building currently). I think I may model the planks and 'assemble' the building again to achieve the desired effect.
Blender 2.73. Cycles. Photoshop for textures.