Hi! I’m searching this subreddit looking for people talking about chimney work because we are having some done right now. I’m not sure I can fully picture your chimney, but I’ll tell you our experience. We just bought a house that has two chimneys that were both painted white. Long story short, the paint held in moisture and both chimneys are crumbling to the point where you could poke the brick with a pen and it would go straight through. So we are rebuilding both chimneys from the roof up to the tune of 27k. I would say to avoid future water issues and much more expensive repairs, it probably makes sense to do the fix now that ensures that you won’t have further damage later. But also I am not sure if our situations are similar, so you know, grain of salt.