Gutters are the kind of job nobody notices until water shows up where it shouldn't. Your mother probably knew which weekend to climb up, or she had someone come out. Now the job has no owner, and that is how water ends up in the wrong place. Give it one.
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Separate looking from climbing
There are two different jobs here. Looking is simple: after a heavy rain, walk the outside of the house with a flashlight and check the gutter edges, the seams, the corners, and where each downspout empties. Climbing is the risky one. Don't let him climb a ladder alone, and don't climb one alone yourself. If the job needs a ladder, hire it out and keep the looking for yourself.
What a complete gutter job includes
Ask every gutter service the same questions and compare the answers in writing:
- Do they clear the leaves by hand, and do they flush water through each downspout to confirm it runs clear?
- Do they check the brackets and hangers, and tell you about any that are loose or sagging?
- Do they take photos before and after, and can you keep copies?
- Where does the debris go, and do they take it away with them?
- Do they check whether each downspout empties far enough from the foundation, and do they say so if one doesn't?
- Do they come back at no added charge if the next heavy rain shows a problem?
Check the downspouts before the cold
Water that sits at the bottom of a downspout can freeze into ice right where you walk. Look at where every downspout empties. If the water runs straight to the foundation or pools beside the back step, ask whether an extension can carry it farther away. Also look for low spots along the gutter that hold standing water between hangers. Standing water freezes, and the weight can pull the gutter loose.
Ice at the roof edge is not a weekend project
After a cold snap, look up at the roof edge. A thick ridge of ice along the eave is a sign to call someone who does roof work and is insured for it. Don't climb up to chip it, and don't pour hot water on it from a ladder. Those are the moves that send people to the hospital.
Name the person who walks the house after rain
Write one line on the household list: who checks the gutters after heavy rain, and who you call if something sags or spills. If that person is you, put a repeating reminder on your phone for the stretch of the year when storms come through your area. If it is a company, write the business name and number on the same page as the reminder.
Let him decide, once you've shown him
He may tell you the gutters are fine because they have always been fine. Walk him outside, show him the one downspout that spills onto the step, and let him decide what happens next. He knows this house better than anyone. Your job is to make sure the decision is written down and somebody owns it.