Train Claude Cowork to fill your multifamily underwriting spreadsheet from the OM, rent roll, and T12
Ben Michel of Ridgeview Property Group spent half a day teaching Claude Cowork his underwriting spreadsheet cell by cell, saved the session as a Skill, and now gets a model populated in about 5 minutes instead of paying a freelancer $100 per property and waiting 3-4 days.
At a glance
- Tools used
- Claude CoworkClaude SkillsExcel
- Category
- Investing & underwriting
- Audience
- investor
- Difficulty
- No-code setup
- Source
- How I Trained Claude to Underwrite Deals
Ben Michel (Ridgeview Report) · Newsletter · Jun 26, 2026 - First step
- Give Claude access to one dedicated folder only and require approval before any file change.
Suggested prompt
Written by this directory, inspired by the source. Replace the [bracketed] parts.
We are filling my underwriting model [file] for the deal in this folder (OM, rent roll, T12). Go one step at a time and wait for my OK after each step. 1. Cell [C11]: find the property address in the offering memorandum (usually the first 4 pages). 2. Unit mix tab: list each unit layout in the rent roll under Unit Type, then fill Unit Count, Average Square Footage, and Average Rent column by column. 3. T12: map each income and expense line to my categories: [e.g. Late Fees -> Other Income; Snow Removal -> Contract Services; Office Supplies -> General/Admin]. Stop and ask when a line is unclear. When we finish, save this workflow as a Skill named "Underwrite deal".