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A gutter system has one job: put the water from the roof somewhere other than against the foundation. In Cypress clay, where it lands matters for years.
Cypress houses sit on slab-on-grade foundations over expansive clay that swells when wet and shrinks in drought. A downspout that empties at the corner of the slab keeps that one spot wet while the rest of the perimeter dries, which is the uneven moisture foundation specialists warn about. It also cuts trenches in the lawn and splashes mud onto brick and siding.
Many production houses were built with gutters only on the front or over entries, or with none at all on some elevations. On those houses, water pours off the eave in a line that shows up as a groove in the flower bed.
A re-roof is the natural time to deal with gutters, because the drip edge and the back of the gutter work together. Ask whether the scope removes and resets the existing gutters or replaces them, and who is responsible if they are bent during the tear-off.
Tell the contractor which corners flood or trench in a heavy rain. That is usually where the work starts.