I like the look of the planking. If you need to re-roof, you could use sheet foam insulation on top of the planking. My shop has an open beam design with planking visible from below. The insulation goes on top of the planking, two layers of foam sheet, 3 1/2” + 2 1/2” to get to R-31, I think. Then 2x4’s going up the slope on top of the foam with spikes driven through the 2x4 and foam into the rafter beams. OSB on top of the create a ventilation channel between the 2x4’s to the ridge vent. Conventional roofing on top of that.