If it's just cosmetic, I'd mask it and bandaid it rather than potentially cause mechanical problems. 

I'd hit it with mud and orange-peel-in-a-can myself while I was doing other maintenance on the property and call it $30.

if the paint isn’t peeling or looks bad I wouldn’t paint If I had to repaint and reroof I would do grey/black roof with light grey paint, black shutters and white trim, red door 

The roof has a leak that has caused the paint to peel off of the kitchen ceiling. 

Standard vinyl clapboard looking siding will peel off easily in high winds.

Looking at a house located in Western Michigan that has cedar siding with paint that is peeling off/at the end of its life.

With all due respect to Joe, it is a huge mistake IMO to let them stay--too much liability and health and safety risk (they really should not even be in there without masks) involved and will massively slow down your remediation and repair process. 

Paint peeled off everywhere they'd put up a Command strip?

(Very small town) She didn’t wear a mask while they were there or let anyone know.

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