Repair or replace
The first thing I decide on any roof is whether it can be repaired. Architectural shingles that are still pliable, with granules mostly intact and no widespread curling, can usually be repaired at the leak point and given several more years. Shingles that crack when lifted, roofs on their second layer, and roofs where the leaks are showing up in three or four places at once are telling you the assembly is done.
I put both options in writing where both exist. A repair is described with what it covers and how long I would expect it to hold. A replacement is described with the full scope. You choose with the facts in front of you.
Ice dams and what actually fixes them
Ice dams form when heat from the house melts snow on the roof, the meltwater runs to the cold eave, refreezes, and builds a ridge that backs water up under the shingles. The fix is not a heat cable, and it is not a new roof by itself. It is stopping the heat loss into the attic, getting the attic ventilated so it stays cold, and putting ice and water barrier under the shingles far enough up the roof that any water that does back up cannot reach the deck.
On a replacement I run the barrier from the eave to well past the interior wall line, across every valley, and up every wall intersection. On the shallow-attic capes in Sixteen Acres and Chicopee, I also address the soffit vents, which are usually painted shut or stuffed with insulation.
Tear-off, decking, and what I look for
I strip to the deck on every replacement. Roofing over an old layer hides rotted sheathing and adds weight that older rafters were not sized for. Once the deck is exposed I walk it, replace any plywood or boards that have gone soft, and photograph the repairs before the underlayment goes on. On the prewar houses the deck is often board sheathing with gaps, and I add plywood where the gaps are too wide for shingles to fasten properly.
Then the layers: ice and water barrier, synthetic underlayment, metal drip edge, starter strip, architectural shingles, step and counterflashing at walls and chimneys, and a ridge vent. Nails are placed by hand where the manufacturer says they go, not blown through the shingle by a gun set too hot.
Rubber roofs on porches and additions
Springfield's flat and low-slope roofs are usually over a porch, a bay, or an addition, and they leak more than the pitched roof above them. I install fully adhered EPDM rubber membrane over a clean, dry substrate, with the seams lapped and sealed and the edges terminated with metal that laps under the shingles above or over the fascia below. Where the old roof holds water, I add tapered insulation or reframe so it drains. A rubber roof that drains lasts decades. One that ponds does not.
Storm damage and the tornado track
The valley gets summer thunderstorms with straight-line winds and hail, and Springfield has not forgotten the June 2011 tornado that ran through the South End, Six Corners, and East Forest Park before crossing into Wilbraham. Storm damage repair starts with a tarp if the roof is open, then a proper assessment of what was lifted, what was punctured, and whether the deck moved. I document what I find in a way that is useful to an insurance adjuster and then rebuild it to a better standard than it had before.
Ventilation, gutters, and the edge
The edge of the roof is where it fails. Drip edge that is missing, gutters pitched wrong, fascia that has rotted from overflow, and soffit vents that do not vent. On every roofing job I look at the whole edge assembly, and if the fascia or the rafter tails need to be replaced, I do that as part of the roof rather than sending you to find a carpenter afterward.