I'm currently working on a product with a team and we did a bit of exploration for an idea for SMB's and had that same issue. We were talking to someone who on the surface would be a perfect fit for the product but then we asked how they handled organizing a job. They reached down into their bag, pulled out a file folder, opened it up and spread a few sheets of paper in front of us and went "will this page is this thing, this one is the other thing, and that one is another thing". An entire jobs worth of documentation and info right there laid out in front of us all at once in 3 seconds flat.
That was the moment we realized the reason our target industry was still using paper and spreadsheets. Because they're not just "good enough". In most cases, they're the best possible option. Maybe with enough iterating and testing we could've come up with a UX that could've put all that information in front of 4 people in one shot that quickly. But the odds are against it and even if we did it would've taken a long time to get there.
A lot of startup founders view "legacy" as a four letter word. But sometimes it's simply the best course. Not everything needs a high tech solution. And accepting that can be really tough sometimes.