CRE Underwriting: How I Built a $4,200/yr System With 1 Folder in 53 Minutes

Ryan “RyMac” McKinney · USMC Veteran · 1 October 2026 · 8 minute read

CRE underwriting software runs $350 a month per person. A brand new member of my free Skool sent me 1 problem in a DM. 53 minutes after my first reply, he had a CRE underwriting system in 1 folder. You can take the same CRE underwriting folder home free.

Here's the DM. September 28th, 3:24 in the afternoon.

Then he told me exactly what he wanted to see. “real MD files, to take it out of "theory" and see it work”

I know absolutely NOTHING about underwriting. I'm a sales closer and a jarhead. I can't write a line of code. I wrote up ICM for people who can't write code because I'm 1 of them.

You watch an example deal walk through his 5 folders live, and the screener hands back FAIL on camera.

What is CRE underwriting?

CRE underwriting is checking whether a commercial real estate deal makes money and whether a lender will finance it. You turn the rent roll, the expenses and the loan into a handful of numbers. Then you hold each number against a floor. Pass or fail.

Lenders do it before they hand over a loan. Investors do it before they make an offer.

Page 1 of Google is written for the lender with a team of analysts. Nobody writes it for the person who wants to screen a deal tonight without buying a software suite.

What CRE underwriting software costs

Smart Capital Center's Professional plan is $350 a month per user on Capterra.

$350 x 12 is $4,200 a year.

DealWise AI is the cheaper 1. 1 charge of $2,136 when you pay for the year up front.

Then there's the top tier. ARGUS Enterprise. Yardi. CoStar. Annual contracts in the $25K to $500K+ range.

His folders don't replace every feature in a full software suite. I'm not going to pretend they do.

They do the job he asked for. Screen the deal. Underwrite the deal. Pass or fail.

And he owns the files instead of renting them. Yes, you still pay for Claude. That's a slice of $350 a month.

The 53 minute clock

My first reply went out at 3:49. That's where my 53 minute clock starts.

At 3:59 I typed 1 line into Claude Code.

I sent him the finished page at 4:42.

I probably only spent 12 minutes of my own time on his folders. The other 41 minutes I was busy doing other stuff for people.

Here's the crazy part. He had already tried to get my free ICM Folder System 3 times that same afternoon. All 3 emails say “Delivered” to his Yahoo inbox. He never saw 1 of them.

So I put the 2 free downloads Yahoo ate right on his page.

He told me “Im not very far along at all...” Another video about folders wasn't going to help him. He needed to see the folders actually work on his business.

The 5 folders a deal walks through

I built his system as an ICM Folder System. ICM is Jake Van Clief's method. He wrote the paper on Interpretable Context Methodology with David McDermott.

ICM is files n' folders set up so that your AI reads the right file first. It's a desk. With a map. And a filing cabinet.

The folders go in the order the work happens.

Every deal lands in 01-Deals-In as 1 card per property.

02-Screen is the 10 minute pass or fail. A deal earns a full underwriting there. Or the deal dies there and you keep your afternoon.

03-Underwrite is the full math for a deal that passed. 04-Stress tries to break the deal on purpose, before the market does. 05-Decide writes the decision down in words, with the numbers next to the words.

The Context drawer holds your hurdles, your market and every source. If you want to see what an ICM folder system is before you open 1, start there.

The live run: FAIL, DSCR 1.03

In the video I run an example deal through his folders live. 24 units on Example Street. $2,400,000 asking. Every number on that card is made up to show the shape.

The screener works 17 numbers in order. Price per unit. NOI. Cap rate. DSCR. Debt yield. Break-even occupancy.

You may hear DSCR called the debt service coverage ratio. It means: does the rent cover the loan?

The broker says the cap rate is 7.2%. Claude gets 5.73%. The broker's NOI is $172,000. Claude's is $137,490. The broker's number is $34,510 too high.

Break-even occupancy came back 95.06%. The limit is 80%.

The verdict is FAIL. The rent barely covers the loan payments, DSCR 1.03. You'd need the building 95% full to break even.

Where does 1.25 come from? Every floor in his folders has a source behind the math. That includes the DSCR floor.

Claude didn't make up 1 floor. Claude read them.

The 4 moves I made in those 53 minutes

If you run an AI agency, this is the DM you want. A stranger in a niche you know nothing about, with 1 real problem.

A web design agency gets these. So does a lead gen agency. Here's the 4 moves so that you can be just as quick on the draw.

Move 1. Find the pain

I asked him a simple question. His answer was “automate my underwriting process and evaluate deals better/faster.”

That 1 sentence told me what to build. His other line told me what “done” looked like to him. Real MD files he could watch work.

Move 2. Research, then folders

Claude read 22 sources on how underwriting is really done. A multifamily underwriting guide. Lender glossaries. Cap rate. Expense ratios. Taxes after the sale.

That way every formula in his folders has a source behind the math.

Then the folders went in the order the work happens. Anything only he could know got marked “ASK” so that Claude asks him instead of guessing.

Move 3. The Loom

He told me he was new. So I ran the example deal through his folders on camera. He watched his folders work before he touched a file.

Move 4. The page

1 page with his folders, the Loom and 3 steps to run them. Plus the 2 free downloads Yahoo ate.

I sent that page at 4:42.

The next day he wrote me back. “wow - reading message from Fred - priceless... thx”

Fred is what I named my Claude.

If you want to sell builds like this to a small business owner, I broke down how to sell an ICM folder structure.

You don't need 22 sources to get your own

His folders came off 22 sources. You don't need to research 22 sources to get a well structured ICM of your own.

So I built the questions into an online form. The Perfect ICM Builder asks you 22 questions in plain English on 1 page. Then your folder is built and your zip is ready to download.

The Perfect ICM Builder demo is in the video.

Questions about CRE underwriting

What is CRE underwriting?

CRE underwriting is checking whether a commercial real estate deal makes money and whether a lender will finance it. You turn the rent roll, the expenses and the loan into a handful of numbers. Then you hold each number against a floor and get a pass or a fail.

What does CRE underwriting software cost?

Smart Capital Center's Professional plan is $350 a month per user on Capterra. That's $4,200 a year. DealWise AI bills $2,136 a year when you pay up front. Enterprise platforms run annual contracts in the $25K to $500K+ range.

What is DSCR in commercial real estate?

DSCR is the debt service coverage ratio. It's the NOI divided by a year of loan payments. It tells you if the rent covers the loan. 1.25 is a common lender starting point.

What is debt yield?

Debt yield is the NOI divided by the loan amount. Most lenders want at least 10%.

Is the CRE underwriting folder free?

Yes. 5 folders in the order a deal walks. The 10 minute screener. All 22 sources. An example deal already in the drawer.

Take the CRE underwriting folder home

I took his name and his market out of the folder. Every “ASK” in there is waiting on YOUR answers.

If you get stuck or confused, come drop a post in my Skool. I will absolutely help you figure it out.

Every ICM Folder System I have built, the free ones and the ones people paid for, is on 1 page.