[john70t]

Is this the roof or siding? Two different things.

I don't know much about cedar except it is a soft wood which is generally rot resistant. A powerwasher can damage it if used too closely.
After a few years, it develops a greyish patina which is nice.

$16K is a lot of money for painting, extremely high I think for the square footage, but perhaps not out of the ballpark.
-Some painters spend a lot of time detailing and lose money on a job. Getting down to the details takes a lot of time if done right. Those guys are true artisans.
-Many just hack it, or subcontract, though.

I'd ask for references to previous jobs and/or owners. The siding isn't going anywhere for now.

Or do it yourself, and buy a new car.