If you're dealing with recurring leaks or widespread damage, it's probably time to consider replacing your roof instead of constantly repairing it. I'd say if your roof is nearing the end of its expected lifespan, typically around 20-25 years, replacement is a better option. You should also look for signs like curled, missing, or damaged shingles, and check your attic for any water stains or daylight coming through the roof. If you've already had to repair your roof multiple times in the past, it might be more cost-effective to just replace it altogether, rather than throwing more money at temporary fixes.