To Replace the Roof or Not?

[Account Closed]

I had 4 different roofing companies assess the roof of my long term rental. All but 3 have recommended replacing the roof completely. It already has 2 layers of shingles, needs a cricket for the add-on chimney, new pipe flanges, flashing, kick-out flashing, and vents. However, it has lasted this long with no signs of leaks. Would you replace it now or hold out until the end of its life?

[Nathan Gesner]

I may not replace it today, but I would certainly prepare to replace it at my earliest convenience. You don't want to wait until it fails and end up with internal damage that costs you even more.