Sunday September 20th 2026 - zoom meeting

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CCIA Meeting Sunday September 20th, 2026

5:30-8:30pm CT

From Listing to Offer in Minutes: A Live Underwriting Walkthrough

With Simon Asselin, Founder relea.ai

Most of us have spent a Saturday in a spreadsheet on a deal we ended up passing on. The real cost isn’t the Saturday. It’s the deal you never got to, because the first investor back with a credible offer got it.

Simon Asselin has been investing for over 20 years across five states, including here in Chicagoland, and he’s a technologist who eventually built the underwriting workflow he wished he’d had. 

In this session he’ll take three real Chicago-area listings and work them on screen, start to finish: 

• The rent roll and what the market actually supports, 
• The expense lines investors get wrong, who really pays the heat and the water, 
• The CapEx hiding in the listing photos, 
• The risks and the due diligence checklist, 
• And finally the metrics that decide it, including how to back-solve an offer price that hits your return target at today’s rates.

Two of the three look good on the listing but don’t survive the underwriting. We’ll go through exactly where they fall apart, and Simon will be candid about the assumptions that cost him money in his own portfolio and how he catches them now.

Bio:

Simon Asselin is a real estate investor of over 20 years with rental property across five states, and a technologist. He is the founder of relea.ai, a kind of "Carfax for real estate investing" that reads a listing, an offering memorandum, county records, and an inspection report and turns them into a full underwriting model in minutes. He built it out of his own workflow, and his own mistakes.

A 2-Minute Walkthrough of the Product

MEETING AGENDA

5:30PM - Informal Networking

• Informal Networking - open discussion and Q/A

6:00PM - Main Meeting

• Benefits & Updates - with Jane Garvey
• CCIA Announcements
• Brief Educational Segment
• Have/Want and Property Presentation

6:45PM:  Main Presentation

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