I'm a software engineer — not a house engineer.

I was trying to buy an 1889 brick two-flat in Chicago — the kind of solid, century-old building this city is full of. The inspection came back with 100+ faults. Pages and pages of them. I could read every line and still have no idea what actually mattered, what it would cost, or how to respond to the seller. I build software for a living; I don't price masonry repairs or read building code for fun.

So I did what an engineer does: I built a tool. It took the inspection apart finding by finding, priced each one against real local rates, flagged what was a genuine safety or code issue versus cosmetic, and turned the whole pile into a single number — and a fair offer I could actually defend. I revised my offer intelligently instead of either panicking or overpaying. That tool became Expresstimates.

Why old homes, specifically

I care about old housing stock. These buildings — the brick two-flats, the workers' cottages, the pre-war walk-ups — are some of the best housing we'll ever build, and they need good people to become their stewards. Too often a daunting inspection scares off a buyer who would have been a wonderful caretaker, and the home lands with a flipper or sits empty.

I genuinely believe that helping people confidently buy and maintain older homes protects our housing stock — and that keeping that stock alive and occupied puts downward pressure on rents and chips, in a small way, at the affordability crunch we're all feeling. That's also why this is priced the way it is: $20 to scout a home, $99 for the full report. It should be accessible enough that anyone considering stewardship of an old home can use it comfortably.

What this is (and isn't)

It's a clear-eyed, sourced second read on what a home will cost you — built to help you negotiate and plan. It is not a substitute for a licensed inspector, appraiser, or attorney, and it never pretends to be. Every figure shows its work.

If you're staring at your own intimidating report — or just want to understand a house before you fall for it — I hope this helps you the way it helped me.

— Harry, founder of Expresstimates