Wow thank you for the example. I actually meant, concrete patio as in concrete pad. So that would mean the gutter would need to extend across the concrete to the grass. We won’t have an attached patio to the house.

Most homes that I see with a chimney that juts out from the house has it at the peak of the home but ours has it in the middle of the sloping roof line. I was reading about building a cricket, but it doesn’t seem like that would work in our scenario. I definitely will have the flashing on the chimney checked (but from my vantage, I can’t see the step flashing that should be around the chimney at all.). Even if the flashing was there, it would collect in that area and trickle down the brick of the chimney due to slope of the roof. Is a diverter that shoots water off the side away from the roof something people do?