Last year we had our roof replaced (I know, a little late of an update there, Megan) after seeing the top of the roof had become something like a spiky fortress wall:

Unfortunately, since our house was a HUD property we have no idea how old the most recent roof installation was (guesstimates say about 20 years) but, as with all things in our home, we learned was just not done well.
A Quick Background of Our Home
Our house is a cape cod built in 1930 and has had probably about a dozen owners with probably half of them happening within the past 20 or so years. Our neighbor next door has grandkids that kinda-sorta owned it at one point, we suspect as either a terrible attempt at doing a fix & flip or as a rental property for tenants who wouldn’t care much about how well things worked, just that they did. Regardless, we have suspicions that every “update” done to our home was done by them, mostly because of the half-assed way we see them care for their own home.
Since we’ve heard it so many times from contractors we’ve decided the slogan of our house is “that wasn’t done to Code.” We’ve dropped probably about $30,000 fixing the work and getting things back up to snuff.
Cue the Roof
So, since our house is coming up on its 100th birthday, there’s a lot of fuck-ups to un-fuck. One of these being the roof.
Typically, houses will have maybe 3-5 layers of roofing on them before there’s a complete tear-off required. Ours, however, not only had 5 layers of roofing but still included the original cedar shake shingles from 1930 still chilling in place. Which we only found out about AFTER the roofers cut a hole in the roof.

Anatomy of a Roof Tear-Off
If you’re about to get your roof replaced and wondering what the process looks like, it goes something like this:
Day 0 – Drop off: Pallets and dumpsters will mysteriously show up in your driveway, though you’re not sure when they got there or why everyone is so quiet and ninja-like about it

Day 1: The teardown begins – The roofers typically start on one side and will knock, pound, swear, and kick shingles off in a “scorched earth” sort of way. This is especially fun when you’re working from home. They’ll also most likely end up laying down the base layer of roofing membrane. For us, since we had the original roof this ALSO required getting plywood boards installed (during the price surge of wood in 2021, of course)
Day 2: The rebuild – This is when the shingles get down. You’ll be surprised at how quickly this goes, considering the number of shingles that need to get installed. This will also be loud but you’re expecting that. You’re also impressed at how no one has fallen off the roof.
Day 3: The finishing – Whatever is left to be done like flashing or smaller roofs (like the one on our porch) is completed. Dumpster is maybe hauled away or saved for another day.
Day 4 – 14 – You wait for the final invoice which for some reason takes FOR.EV.ER.
“You don’t sound super-happy about this project, Megan”
You’d be correct! Having a roof redone from scratch is a project and a half, especially during the pandemic AND materials price surge. Our 1380 sq ft house warranted a cost of $13,000 for the roof tear-off. Which, so be it, EXCEPT the contractor tacked on costs for the plywood after discovering the original roofing still existed and is something he should have caught first (to give credit where it’s due, he did admit he screwed up). However, he also tried to add on more charges that weren’t in the contract and complained repeatedly how he only made “a few bucks” on the project which was…not our fault?
How’s the roof look now?

Admittedly, it’s in good shape. I picked a dark gray shingle (sorry, don’t remember the SKU) with blue flecks in it to complement the blue siding and shutters on our home. There’s a slight bulge at the top of the roof I don’t remember having before (behind the dormer in this pic) but Steve says it’s fine (which is why I took off a point in the review score). We have a 20-year labor warranty but doubt I’ll ever reach out to that roofing company should something go wrong.