Get seamless gutters — Sectional gutters leak at joints over time. Seamless gutters are cut on-site, cost only 10–15% more, and have far fewer problems long-term.
Replace in fall after leaves drop — Installers have more availability Oct–Nov and you can clean/inspect at the same time. Avoid spring when demand peaks.
Bundle with roof work — If getting a new roof, negotiate gutter replacement at the same time. Roofers discount combo jobs 10–20%.
Gutter guards aren't always worth it — In areas with light tree cover, guards cost $500–$2,000 but save only $150–$300/year in cleaning. Do the math for your yard.