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Signs your roof needs work, and signs it does not
You cannot see your roof, which is exactly why standards slip and why people worry about the wrong things. Here is what is worth acting on.
From the ground, with binoculars
Look along the ridge line and the eaves line. A dip or a wave in either suggests movement in the timber under the covering, which is the one visible sign worth taking seriously straight away.
Look for gaps where a slate or tile has gone, and for units that have slipped down the slope. One or two in a cluster is a repair. Several, in different places, appearing again after each gale, is nail fatigue across the whole roof.
Look at the mortar where the roof meets a chimney or a wall. Cracked or missing fillets are the commonest cause of the leak nobody can trace.
From inside the loft, on a bright day
Turn the light off. Daylight through the covering is not always a fault on an older slate roof, but daylight in one specific spot usually is. Look at the underside of the deck for dark staining, and feel the rafter ends where they meet the wall for softness.
Check whether the insulation is blocking the ventilation path at the eaves. If it is, and the loft smells damp in winter, you may have a condensation problem rather than a leak, and no amount of work on the outside will fix it.
Things that worry people and usually should not
Moss. On many roofs it is doing no harm at all, and aggressive pressure washing does far more damage than the moss ever would. It matters where it is holding water against the covering or blocking a valley, and there it gets removed carefully.
A single stain on a ceiling that has not grown in two years. Old, dry, and usually the fossil of a repair somebody already did.
Your neighbour having a new roof. Houses in a terrace were roofed at the same time but they have not weathered identically, and a salesman knocking after doing next door is not a diagnosis.
Things worth a call today
Water actually coming in. A stack that has visibly shifted. A section of covering lifted after a storm. A gutter overflowing down a wall, because that damage compounds every week it is left.
Everything else can wait for a considered look rather than an emergency one, and you will get a better job for it.
Questions
How often should a roof be looked at?
Once a year for most houses, and after any serious storm. Where there are trees, valleys or box gutters, twice.
Should I let somebody who knocks look at my roof?
Not on the spot. Take the details, then decide in your own time and get a second opinion. Nobody legitimate needs you to agree today.