We Asked Santa for a New Roof — Instead, We Found a Roofer Unlike Any We’d Met Before

So this year the Gusman and I had a conservative Christmas because unless Santa delivered us a new roof, we were going to have to break our piggy bank to pay for a new one. So I reached out to my wonderful Editor Shelby Skrhak and asked her if she would be interested in me recording our endeavor to find a roofer. Being the smart woman that she is, she said would be interested in such a story and let me tell you it will not disappoint.

When my husband Gus and I purchased our home in historic Elm Thicket/Northpark back in 2007, the inspection report was thick. The pier-and-beam foundation was in great shape. It was everything else that needed TLC.

We knew very little about remodeling, so we hired a contractor to help us redo our cozy two-bedroom, one-bath home. We learned a lot, mostly that we would be our own contractors for any work we needed in the future. The biggest issue we had with our new roof were leaks. They have been the bane of our existence ever since that time.

Over the years, when a leak appeared, we’d call a roofer, they’d make a repair, and we’d move on until the next leak made its presence known. No one could give us a definitive reason why the leaks kept happening. We were told a nail had popped up, or that the wind must have blown water under the shingles.

Fast forward to September 2025: Our insurance carrier notified us that our roof had failed their inspection and that, unless we installed a new one, they would cancel our policy. We did not put up a fight, but that meant finding a roofer we could trust.

In all honesty, I lost track of the number of roofers we had traipsing along on our roof. It’s a 1,000-square-foot home with an added back porch covered in roll roofing. When the roof was first replaced, the contractor chose roll roofing for the porch — sold in large rolls and typically used for low-slopes — because shingles were not an option. That detail becomes important later.

Over the next two months, every bid we received differed in the scope of work, the materials proposed, and even the measurements. Some roofers never submitted a bid at all, while others sent one without ever looking at the property. The bids we did receive ranged from $10,000 to $15,000. The only thing that was consistent was that they all wanted a signed contract. One company even contacted us to ask if we’d made a decision, even though they had stood us up.

We went to the Better Business Bureau, asked friends, and scrolled through Nextdoor looking for recommendations. No one had won our trust.

Okay, are you ready, because here comes the really fun part of this story.

When I went for my haircut in December, my stylist asked how we were doing. I said, “Amy, we need a new roof, and I’m at a loss.” Her response: “I have the greatest roofer for you. She is a professional make-up artist, but also has a roofing business. She knows how to make everything beautiful. You’re going to love her.”

I didn’t know if I was going to love her, but there was no way I wasn’t going to meet a professional make-up artist who also happens to be a roofer. And honestly, I’ve learned to always trust my stylist, Amy.

On New Year’s Eve, I called April Santiago with Bootstrap Roofing and gave her the same information I had provided everyone else. The first thing she did was pull a GAF roof report, which provides detailed measurements, material estimates, and visualizations. For $20, I learned the exact measurements of our roof — something no other roofer had mentioned. For an additional $10, she pulled a hail and wind history to see if the replacement of the roof was necessary due to weather damage.

That’s when I knew April was going to be different. She planned to follow the GAF report recommendations exactly, which meant there would be no question of ordering extra materials or being billed for something we did not need. In other words, we were finally working with someone we could trust.

Next came the in-person inspection, the bid, and the moment of truth, which is where this roofing adventure really begins. We’ll get into that tomorrow.