We've had Cedar Shakes on the house I live in Dad built in 1953, and addition we added on in '64. Holding up great, but, need to be stained every 5 years or so.
I would say the most important factor would be the stain. If you are going with a colored stain, check to see if you can purchase a 100% oil base stain, not latex, something that will soak in the wood, to help preserve it. I will have to say it is better for bonding to the wood also. I'd advise not to buy the less expensive brand to save a few bucks, it could come back to bite you. The first oil stain that was put on, was made by Sherwin-Williams, and was great stain. Sometime in the 80's, they quit making it, probably due to the aluminum, and vinyl siding craze. A local hardware carried a decent brand oil stain, and it also seemed to hold up well. About 8 years ago, I went back to the same hardware, and got what I thought was the same product. Within 5 years, everything facing direct sun exposure, started rolling off. It wasn't due to high humidity, it was put on in Sept., our usual painting time when the humidity in low. Every other side of the house that doesn't get direct exposure was fine.
2 years ago, it was time to re-stain. Thanks to the internet, and a lot or reading on products,and their reviews, I finally decided on Cabot brand oil stain. Doing some checking, I saw 2 versions of the same product, so called the Cabot help line, to see what the difference was. The Rep explained that due to VOC laws passed in certain states, you are not able to buy 100% oil stain. But, their product is a "water encapsulated" oil stain, which I did not comprehend. She told me, "Imagine a bubble of oil stain, surrounded by a bubble of water. When you brush it on, brushing bursts the bubble of water, evaporating off, leaving the oil stain" I found that I could buy the 100% oil stain in a neighboring state 2 hours away, and thought it would be worth the trip to get it. She told me I could, but don't be caught with it here in this state, as there is a $10,000.00 fine, if they do. PER GALLON... In my mind, I kept picturing being in an accident, and a can popping open, Haz-Mat being called in, and me facing a $180,000.00 fine, so went with the water encapsulated.
I wire brushed, and wore out 5 stainless steel wire brushes, and 4 small screwdrivers cleaning the little grooves in the textured shingles, which took 4-5 time longer than the actual application of the stain. Due to the brushing, some bare wood was exposed, and routed out the soft cell layers in the wood. The first coat dragged hard on the brush. And, when filling the open cells, they would fill when brushing in one direction, and pull back out, brushing back the other way. VERY frustrating..!! I am assuming, due the the water encapsulating, and breaking that water bubble. However, the second coat went on, very easy, or as I would expect a 100% oil stain should.
I just re-stained a small building last week, going through the same process on it. I'd originally got enough stain to do the house, and that building. But due to the length of time it took to do the house, cool weather caught me, so put it off to last year. And last year,due to it raining most of the summer, through Sept., it got put off another year. We had the perfect weather for it, so got with the project. After finishing, I stood back, and compared the color. In 2 short years, it seem the pigment has faded a bit on the house, even in the not directly exposed to the sun sides. When doing the house 2 years ago, I got wire brushed down to the original Sherwin-Williams, and it's color
was as brilliant, or looked to be, compared to what was right beside it, of coats of other later brands. Sure seems to me, they sure don't make it like they used to.