I get where you’re coming from—waiting until something fails can feel like tempting fate, especially with older roofs. Those original vent boots from the ‘60s are probably past their prime, even if they look okay on the surface. Rubber and plastic just don’t last forever, and UV exposure really does a number on them over time. I’ve seen boots that looked fine from the ground but were cracked or brittle up close.
Moss is another wildcard. It holds moisture against the flashing and can hide small gaps, like you found. That’s usually how slow leaks start—tiny cracks that go unnoticed until there’s real damage inside. Personally, I lean toward proactive replacement of things like vent boots every 10-15 years, especially on low-slope roofs where water doesn’t run off as fast.
Full roof replacement every decade seems a bit much unless you’re in a really harsh climate or have major issues. Patching as needed works, but only if you’re diligent about inspections. Peace of mind is worth something, though... sometimes spending a little now saves a lot of hassle later.
Swapping out vent boots every 10-15 years makes sense, but I think there’s a more sustainable angle that gets overlooked. Instead of rubber or plastic, I’ve started using silicone or even metal retrofit boots—they cost a bit more upfront but last way longer and handle UV much better. I get the urge to replace on a schedule, but if you’re already up there, why not upgrade to something that might outlast the next set of shingles? Less waste, less hassle down the road. Just my two cents from too many weekends on the ladder...
I get where you’re coming from with the scheduled swaps, but honestly, I’m with you on the upgrade route. I used to just grab the cheapest rubber boots at the hardware store, thinking I was saving money, but after a couple of brutal summers here in Texas, they’d start cracking way before the 10-year mark. The last time I was up there patching leaks, I switched to silicone boots—yeah, they cost more, but I haven’t had to mess with them since.
Metal’s even better if you don’t mind the look, especially on a steeper roof where water runs fast. Less plastic in the landfill, less time on the ladder, and fewer surprise leaks during a storm. Only thing I’d say is double-check the fit if you’ve got odd-sized vents—some of those retrofit kits can be a pain if your pipes aren’t standard.
In my book, spending a little more upfront beats crawling around up there every few years. My knees thank me for it.