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Need advice on replacing an old leaky roof

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(@astronomy241)
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Either way, flashing is the real MVP. Skimp there, and you’re just asking for headaches, no matter the material.

Couldn’t agree more about flashing—seen too many “premium” roofs leak just because someone cheaped out there. Had a job last year where the homeowner wanted metal for the look, but their roof was all hips and valleys... install was a nightmare. Ended up recommending high-end shingles with proper ice & water shield, and it’s been bone dry since. Sometimes simpler is better, especially if your roof isn’t a basic gable.


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(@donnariver35)
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Sometimes simpler is better, especially if your roof isn’t a basic gable.

That’s been my experience too. I’ve lost count of how many times I’ve watched folks get talked into “high-end” or trendy roofing systems that just don’t suit the actual roof shape. Hips, valleys, dormers… all those details are where leaks love to show up, and if the flashing isn’t done right, it doesn’t matter what material you’re using.

One thing I’ll add—sometimes people focus so much on the visible parts (shingles, tiles, metal panels) that they forget about what’s underneath. You mentioned ice & water shield, which is huge in colder climates or anywhere with tricky roof geometry. I’d also say pay attention to ventilation and attic insulation while you’re at it. If you’re already tearing off the old roof, it’s a good time to check for any signs of moisture in the decking or mold up there.

I’m curious—when you switched from metal to high-end shingles for that job, did you run into any issues with the homeowner being disappointed about not getting the “look” they wanted? Sometimes I find people get really set on an aesthetic even if it’s not practical for their roof style or budget.

Also, have you ever tried one of those synthetic slate or shake products? I’ve had mixed results—looks great from a distance but sometimes the install gets complicated around valleys and transitions, just like metal.

If anyone else has tackled a complex roof recently, did you stick with traditional materials or try something new?


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(@business_diesel)
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Sometimes people focus so much on the visible parts (shingles, tiles, metal panels) that they forget about what’s underneath.

- Had a similar situation last year—client wanted cedar shakes for the “storybook” vibe, but their roof was all hips and valleys. Ended up convincing them to go with architectural shingles and invest in better underlayment instead.
- They were a little bummed at first, but once they saw how clean it looked (and how dry the attic stayed), they were sold.
- Tried synthetic slate once—looked amazing from the curb, but the installer had a nightmare with all the weird angles. Not sure I’d do it again unless it was a simple roof.
- Honestly, sometimes less is more. The right details underneath matter way more than what you see from the street.


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(@elizabeth_johnson)
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You nailed it with the underlayment focus. People get really hung up on aesthetics, but if the roof deck and underlayment aren’t solid, it’s just lipstick on a pig. I’ve seen “premium” roofs leak because the installer skimped underneath. I get the appeal of cedar or fancy synthetics, but on complex roofs, practical choices really do save headaches (and cash) down the line. Sometimes I think homeowners underestimate how much those hidden layers matter... until the first big storm rolls through.


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(@gadgeteer888174)
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if the roof deck and underlayment aren’t solid, it’s just lipstick on a pig.

Couldn’t agree more. I’ve inspected roofs where the shingles looked flawless, but underneath, the sheathing was rotted or the underlayment was barely there—total disaster waiting to happen. On steep pitches or valleys, I always recommend ice and water shield, even if local code doesn’t require it. It’s not glamorous, but it’s what keeps the “fancy” stuff above from turning into a liability. People get fixated on the visible layer, but honestly, the real value is in what you don’t see.


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