Got chimney. Where's your saddle?
You wonder about chimney guys and roofers? Whose responsible for ensuring there's a saddle (aka cricket) behind wide chimnmeys to force the water running down the roof to go around the chimney instead of overrunning the chimney flashing and leaking into the house.
I can kind of understand it on old houses where they may not have "done it that way".
But the new technology and ideas for preventing roof leaks call for saddles behind wide chimneys.
Here's an example:
Does your wide chimney have a chimney saddle (aka chimney cricket) behind it?
If it doesn't, you might want to think about getting a roofer to install one to prevent future water damage.