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Hi Tim,
Harry's post is worth considering on two points: There is NO way to access the condition of your roof from what you have posted, and, the water intrusion seems to be isolated to the roof/wall joint(s). Your shakes do not look all that bad! Have your licensed, reputable, qualified roofer come and look a those details as well as the entire roof.
Here is a small primer I have for shake roofs.
Shake roofs have an average life expectancy of 25-30 years. The interesting thing about shake and shingle roofs is that each piece of wooden roofing material is a unique individual! One shake can look fine, the one next to it can be in need of replacement. That can be a neat way of "stretching" the life of the roof. Cedar shake and shingle roofs that are given "tune-ups" about every 3-5 years can last a very long time indeed!
Here are some of the conditions that would indicate a shake roof would need to be replaced:
Vertical splitting( especially excessive splitting), Sun worn to the point of being unreliably thin or has holes/deterioration due to sun. Deteriorated butt ends past 1" up from the bottom of the shake. Cupped and curled shakes. The shake is missing. The shakes and/or under/overlayment were not installed correctly
The "sunny side" of the roof ages faster and needs more maintenance in general. If there was no preservative applied when the roof was new; it will do no good to apply it this late in the life of the roof. A shake roof tune up can cost a few hundred dollars.
A new roof would probably be a composition shingle roof. That means extra expense to strip off the shakes and then put down a solid sheathing to accept the shingle roof assembly I would call a licensed, competent roofer and ask them if they have experience with doing shake roof tune ups. Have them come out with the idea of doing typical repairs and after they give you an estimate for repairs, ask their opinion as to a projected life expectancy if they feel it does need to be replaced.
Please let us know wha thappens!
Thanks all, hopefully hearing today on the offer, then onto inspection and roofer quotes. I'll keep you all updated. I was doing some research last night and came across metal shakes, now they look like a nice alternative. I don't think the HOA has any real sway over the roof, several of the surrounding houses have composite shingles. I believe the roof is about 20 years old so it is probably near the end of it's life and also the photos were from the sunny side of the house, the backside looks fine!
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