The most cost-effective time to install or replace a skylight is during a roof replacement. When your roof is already being removed and replaced, adding a skylight saves $500-$1,000 compared to standalone installation because the roof opening, flashing integration, and material transitions are handled as part of the larger project.
If you're considering a new roof in the next 1-2 years and want skylights, wait for the roof project. If your existing skylight is actively leaking, don't wait — repair it now to prevent interior water damage, and we'll ensure the repair integrates properly when the new roof goes on.