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Some folks make beer out of that tree. Crushed twigs smell like wintergreen.

Roof does appear to be holding water, but more like ponding due to sag than poor drainage. Sell them gutter cleaning anyway :)...can't hurt.

The little section of bark showing could be cherry but the wood is white so imo can't be cherry. Wood looks like maple but not the mossy bark

Cherry is my guess. The roof looks like it’s holding water. Maybe up sell a gutter cleaning.

Hard for me to tell what kinda tree that is, Give a hint or maybe pick from 3. Looks like tulips beside the house.

I learned that from a fortune cookie. Lol

That lead doesn't look terrible in the photo, but Rajan speaks wisely.

I’m not a fan of climbing growth from a topped tree. A lift rental could be an option.

...bought his first house recently. He is concerned about a tree partially overhanging a garage. I offered to look at it and prune or remove *if* I was confident that it was within my limited capabilities. I got the first picture today but have not yet viewed it in real life. Garage is on the...