The leeward side of the tiny house has a much steeper roof and much shorter walls. The walls are only 6 feet high, yet the roof reaches 13 feet! This means that the majority of the leeward wall is going have angled ends to the siding planks.
The plank above the window is the last piece that has straight ends, all the planks above this one will have beveled ends to accommodate the pitch in the roof. From a visual point of view, it is best to make this plank a continuous one with no butt joints. This plank will receive considerable visual attention and a butt joint will draw the eye to the blemish instead of blending in with the rest of the wall. The butt joints are visible in the lower planks, but they blend in with the rest of the wall below the window.
The planks are all set, measured, and cut to maintain a three inch gap between the end of the plank and the roof line. I also avoided butt joints in the pitched part as they would only add complexity to the beveling process of the siding installation.
The siding proceeded quickly and with no hard labor. The only added complexity to siding this part as compared to the lower (square) part was the additional trips up and down the ladders. These trips up and down simply add steps to the installation and steps take time. On cold fall days, daylight is a limited resource so time is of the essence. Once the sun sets, the temperature drops and working conditions become unbearable (for me at least). To reduce working times, having all of your tools set up and materials right by the house keeps the amount of walking under control and helps increase efficiency which decreases installation time.
Siding is not rocket science, it just requires repeatable and consistent working. This will produce a uniform looking job that will last for years.