The type of finish selected is driven by style preference.
Painting cedar roof shingles.
Any rough treatment in your preparation will damage the visual aspect of the material as it is cedar which is a softwood.
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I preferred stain over full bodied paint on rough cedar sided homes because it put less build on the home.
Cedar shakes are cedar shingles that naturally weather and are resistant to decay.
Further the less build up of paint stain film the more the house can breathe and the less the chance of moisture related peeling.
The cedar shake shingle bureau a nonprofit trade organization warns that an experienced washer should assess a cedar siding job individually since high pressure water jets can damage wood.
Choose the correct type of paint for the cedar.
As with all painting surface prep is the key to success.
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It is not all about protection.
Up to 40 year warranty.
New cedar shingles are more frequently stained than painted but painted wood shingles are much less maintenance intensive.
Painting weathered cedar shingles goes hand in hand with new ones.
Paint cedar for a more formal look.
For many owners painted cedar siding is a particular style.
It does not conceal the texture of the rough sawn lumber.
See costs licenses and reviews from friends and neighbors.
Exterior grade acrylic latex paint is the most dependable finish in terms of protecting cedar.
The paint will begin to peel and the shingles may become stained and they will need to be repainted.
Stains will only hold up on cedar shingles for two to three years while a quality paint will serve as an attractive finish for 10 to 15 years.
They consist of a layer of cedar mounted to either plywood or fiberboard and are attached in panel form.
Quality repairs patches new roofs replacements.
Only exception to this is weathered shingles require power washing removing old decayed wood layer off.
Your problem looks more like an issue of poor preparation between previous paint jobs.
Like most wooden shingles however especially when painted they require care and maintenance over the course of time.