You will need to do prep work and repairs to your home’s trim, etc. regardless of what you choose to do. You understand that the rotting boards, etc. will have to be replaced even if you side with vinyl. I have a century home that is sided in cedar. We have owned it for 30 years. We have had it painted four times, and each time we have had wood repaired or replaced. With wood. It is inevitable. With each repainting, we have noted, the paint seems to last longer. Better paint formulations have helped. And quality workmanship by out painter. (The same man has painted the house the last three times!). I suggest that you repaint your home, keeping the cedar and replacing the rotted, damaged wood. Don’t skimp on the paint OR the labor.
Q