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Mics has the best solution, a cold attic. But it's hard to do especially with some two story houses without an attic. Here in Maine this is a very very common problem. Roofers have a rubber sheet they put on under the first several rows of shingles that help. But, from what I can see the roofs still will often leak or at least leak after a few years. Oh, BTW, gutters make it worse. As the snow builds up it crosses over to the gutters and the gutters help hold the ice on the edge.

Here is How I never, ever have any roof leaks. (beyond doing what Mics said above). When installing a roof or repairing one; on the first 6 feet. I put felt paper like usual then I put a row of roofing paper. That's the thick stuff but not the one with the rocks. Place it with few nails and tar the nails. Then overlap another sheet and roll it out but tar 6" where they overlap. Then… seal the edge of the seam again with tar. Next, lay your shingles but tar a few inches of the top half of the shingle that doesn't show being sure to completely tar the nails on each shingle. So you end up with shingles that are sealed from on row to the next. Tedious but it's only a few feet. It looks from the picture that you'd have a lot of short roofs and porches to do so you'd have to do this process for all of these.

The other solution is to install a steel roof. They really look nice now but are fairly expensive. Interestingly the material is not that much and the one or two day installation is what costs. i.e. a roof that might have $2000-$3000 in materials could cost 8000-10000 total. Steel roofs are easy to put up. You can find directions online in many places.

I'm not a roofer or even a contractor but I've put on both shingle and steel roofs for myself and relatives and a few paying people who wanted one of my roofs because for some reason Mine was the only one on the street that didn't leak.
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