Milwaukee is a city of every kind of home. Million-dollar houses on the lake, brand-new construction, little ramblers and salt boxes, and a whole lot of very old homes that have stood for a hundred years. This is a story about one of those old homes, a man named Charlie, a city inspector circling like a hawk, and a decision about whether to do a job the right way or not do it at all.
The man in the bush
I pulled up at ten on a cool October morning. The house was old and it was rough. From the street I could already see the roof was in real disrepair, the soffit and fascia were rotted or missing, the front porch and stairs didn't look structurally sound, and the front window on the second floor was completely rotted out. This was a home in trouble, no question.
I walked up the sidewalk and noticed a man in the bushes. Not next to the bushes, in them, sawing away at some branches. That was my homeowner, and his name was Charlie. Now I'll be straight with you, based on how things looked, my first thought was that this fellow might be a squatter, not the owner. I was wrong, and I was about to be wrong about a lot. Charlie turned out to be one of the most unique people I've ever met, and one of my favorite customers and projects I've ever had the honor to be part of. Words don't quite do him justice.
A house on the city's list
Charlie had called us out about the roof. After a long walk around the property, the real story came out. A city inspector had found the home and zeroed in on it as a candidate for condemnation. Charlie and his sister lived there, in a house that had been passed down from his grandparents, and he was not about to let the city take it. He'd been handed a list of things that had to be fixed immediately or the house would be condemned.
So what did I have in front of me? A very unusual man, a dilapidated home on the edge of condemnation, and a mountain of work standing between Charlie and losing the house his family built their memories in. Where do you even start?
Done right or not at all
I was straight with Charlie from the driveway, because my first read was that this might be a bulldozer job. I told him, Charlie, just to pull this roof off, we're going to have to rebuild the roof structure itself, I can see that from here. And I have to be able to warranty it. If I can't warranty it, I'm not doing it, I don't care what you pay, because it isn't worth it to either of us. So if this is going to be anything at all, understand it gets done right or it doesn't get done.
To my surprise, Charlie looked at me and said, that's the straightest anybody's been with me since this whole thing started. He said, I don't care what it costs, I know it won't be cheap. I love this home and I want it fixed. Help me save my home.
That was the whole deal, made right there in the driveway. Not on price. On doing it right.
Got a roof or a home the city, an inspector, or another contractor has you worried about? Book a free assessment. We'll tell you straight what it really needs, and whether it can be done right. If we can't do it right, we'll say so and help you find who can.
What we found when we opened it up
Once we started stripping the roof, the house told the rest of its story. There were four layers of roofing up there. Two of them had been applied improperly over the years to cover up damage instead of fixing it, and one of the layers was asbestos that had to be remediated before anyone could go further. Roofing over problems is exactly how a house ends up like this, buried under layers, rotting quietly underneath.
We ended up having to completely rebuild the roof deck, the soffit and fascia, two dormers, all the gutters, and the entire exterior of the addition off the back. This was far beyond a reroof. To do it right and to code, we brought in three separate specialty crews alongside our own, one to handle the asbestos remediation, one to reframe the dormers and the rear structure, and one to do the structural work on the front deck so it would pass inspection. If you want to understand why that asbestos layer couldn't just be torn off, I told that whole story in the asbestos siding piece, and it's the same rule for a roof.
When we take on a project, we make a commitment to the homeowner. Done right, or not at all. We followed that all the way to the end on Charlie's house.
Getting to know Charlie
Along the way, I got to know the man, and I'd call him a friend to this day. It turned out Charlie is a well-known musky fisherman, and if you live in Wisconsin you know that's no small thing around here. He's the real deal on the water. I even walked away with a few of his lures, and I get to say I rebuilt the home of one of the best musky anglers around. What a job I have.
When we finished, the home looked incredible. Not new, because this was a 1920s Milwaukee house and that's not the point. Revitalized. A home with a new lease on life, and a city inspector who had to go find somebody else's house to worry about.
The settle-up
On my last visit, we were sitting in his living room, on lawn chairs, because Charlie was Charlie, and it was time for him to sign off on his completion certificate. He signed it happily, then looked at me and asked, do you take cash?
The project came to just over $60,000 all in, and he'd put 30 percent down with a bank check, so I figured he meant another check. I said sure, Charlie, no problem. Then he got down on his hands and knees in front of his chair, reached into a hiding spot, and pulled out a roll of cash like I'd never seen in my life. Turns out Charlie was raised on a simple rule: if you can't pay cash, you don't do it. So he paid in green. I will tell you, the drive back to the office with that much cash in the truck had my knuckles a little white, but we got it there and it all ended well.
Why I'm telling you this
I pulled up to Charlie's house ready to write it off, and him with it. I left with a friend, a rebuilt century home, and a reminder I carry into every driveway. We love our customers, all of them, and no matter who's on the other side of the door, we'll tell you the truth and give you the right path forward. And if a job can't be done right, we'll tell you we can't do it, and we'll help you find the people who can.
If you've got an older Milwaukee home that needs real help, not a cover-up, that's exactly the work we live for. Take a look at our roofing, read why the cheapest quote usually costs the most, or book a free visit and we'll tell you what your home actually needs.
Old roofs, layers, and doing it right.
How many layers of roofing are allowed on a home?
Building codes generally limit a roof to two layers of shingles. Going beyond that is typically a code violation, and it piles dangerous weight onto the roof structure while hiding the damage underneath. On Charlie's home we found four layers, two of them added improperly to cover up problems rather than fix them.
Can you roof over old layers or asbestos material?
Roofing over old layers to save money is exactly how homes end up with three and four layers and hidden rot. And if any of that material contains asbestos, it can't simply be roofed over or torn off by a regular crew, it has to be handled by a certified asbestos abatement contractor first. The right path is a full tear-off, remediation where needed, and a rebuild of whatever's damaged underneath. More on that in the asbestos story.
What happens if the city flags my house for possible condemnation?
A city inspector can issue a raze-or-repair type order that lists what must be fixed to keep the home from being condemned, often on a deadline. It's stressful, but it's usually fixable with the right contractor. Get someone qualified out quickly to scope the real work, confirm it can be done to code and warranty, and start knocking out the list.
Do you rebuild the roof structure, not just the shingles?
When it's needed, yes. A roof is only as good as the deck and structure under it. If the deck, framing, dormers, soffit, or fascia are rotted, they get rebuilt as part of doing the job right. Shingling over failing structure isn't a repair, it's a cover-up that fails again.
Got an old home that needs real help?
Book a free, no-pressure in-home assessment. We'll tell you straight what your roof and home actually need, and whether it can be done right. That's the only way we do it.