That is looking good. Where did you use the roof planes? I find it is all about adjustments and sometimes one way works better than another. Sometimes a hidden (not extracted in 3D) beam or two does best. Sometimes multiple roofs with holes are needed. Moving references off to hidden walls or beams outside the plan sometimes works too.
Another option for the gable siding is to extend the overhang of the top window trim piece so it covers the gable. Also, you can place another wall (siding only) with offsets to be on top of the window trim (I usually will make that wall hidden and set the wall joins to '0') and then set that wall to fit to roof as well. Pull the new shake wall out just 1/2" or so to sit in front of the main wall. Or, set up your wall definition to have each siding and trim banding at the exact locations you want for that particular wall. It takes some adjusting, but it works too. You can either do the trim with the window, banding, interior trim, or in the wall definition. Lots of options, just have to try out different ones to see what works best for you and how you want to present your drawings. Once you decide on the way you want, you always need to check to be sure the materials are extracted and checked to show up in elevations and renderings.