Over the last 15 years I have been walking my shake roof every year and replacing pieces as needed. This is a good day's job but it has kept the roof in good shape and stopped having to re-roof the whole thing -- which requires a city permit which means a nosey inspector, a permit fee and an increase in the annual property taxes. None of this if you just replace a few at a time.
I generally carry an armful of shakes, and drop one every time I see a loose or damaged piece. Then go back and install them. Not that hard to do.
Last time I was on the roof, I put up an antenna, got a little dizzy and did a couple of pirouettes. So I decided it was time to look into supervising from a lawn chair next time.
For these kind of jobs, the guy who comes out is different from the half-drunk feller who comes out to do the work. Or they send someone who can't understand the language with no translator. The one and only time I did this, the guy cut down a rose bush and a grapefruit tree. The bad part about it is that ten years later I am still hearing about it....
Anyway, I don't know where this is leading. Just a pain having to find someone without a referral I guess....