People notice the roof less on sunny days, but sunny days are when fixing it is easiest.

The roof is easiest to fix when it is dry, and that is precisely when nobody thinks about it. By the time the need is obvious, the conditions are worst: it is raining, damage is happening, and the repair is urgent and expensive. Good times are the working window and they are usually spent enjoying the weather.

Do the difficult maintenance during a calm period. Have the conversation, get the check-up, fix the thing while nothing is wrong. That is what calm periods are for.