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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Property taxes are one of the biggest frustrations for Chicago real estate investors, landlords, homeowners, and small business owners.
Most people know their bill went up. Fewer people understand why it went up, how the assessment system works, what the Cook County Assessor actually controls, and what can be done to make the process more predictable.
In this episode, Tom Shallcross and Mark Ainley sit down with Pat Hynes to talk about Cook County property taxes, assessment transparency, appeals, data accuracy, development, stadiums, and why predictability matters so much for investors.
Pat brings decades of experience in property assessment, appraisal, and local government. His message is clear: Cook County does not just need lower taxes. It needs a more understandable, more predictable, and more accurate system.
For Chicago investors, the biggest takeaway is that property taxes are not just an expense line. They affect underwriting, affordability, development, rent growth, and whether people choose to keep investing here.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Check your property details on the Cook County Assessor’s website. Make sure the characteristics are accurate, including things like garages, square footage, bathrooms, units, and other property details. Bad data can lead to bad assessments.
Q: What is Pat Hynes’ background?
A: Pat grew up on the South Side, worked in real estate appraisal, spent more than 20 years at the Cook County Assessor’s Office, later became Lyons Township Assessor, and has deep experience in property valuation.
Q: What does Pat think the assessor’s office needs to improve?
A: He wants to get back to the basics: accurate data, clear communication, predictable assessments, and a system taxpayers can understand.
Q: Why are Cook County property taxes so confusing?
A: Pat explains that Cook County has a more complicated system than the rest of Illinois because it classifies property differently, especially between residential and commercial property.
Q: What does the Cook County Assessor actually control?
A: The assessor determines market value for properties. The assessor does not control the levy, school budgets, municipal budgets, or every line item that appears on the final tax bill.
Q: How can the assessor still influence tax bills?
A: Pat says growing the tax base matters. If Cook County encourages more development and more taxable property, the tax burden can be spread across a larger base, which can help put downward pressure on rates.
Q: How does Pat want to use technology and AI?
A: He wants to improve property data by using available online information, photos, sales data, leasing data, and taxpayer-submitted information to better understand the actual condition of properties.
Q: What should investors look for when reviewing an assessment?
A: Start with the basics: square footage, number of units, bathrooms, basement use, exterior construction, condition, income assumptions, cap rate assumptions, and whether the property description is accurate.
Q: Does Pat think every owner should need an attorney to appeal?
A: No. Pat says the system should not be so complicated that every taxpayer feels forced to hire an attorney. His goal is to make the appeal process more understandable and easier to navigate.
Q: What does success look like for Pat?
A: In the short term, he wants to reduce volatility and make property taxes more predictable. Long term, he wants to expand the tax base, encourage investment, and put downward pressure on individual property tax burdens.
Show Notes
02:01 Housing provider tip: check your property characteristics on the Cook County Assessor’s website
02:50 Pat Hynes’ background in Beverly, appraisal, property management, and assessment work
05:26 What the assessor’s office looked like decades ago and why Pat wants to get back to the basics
07:29 How Cook County’s assessment system differs from the rest of Illinois
09:16 The biggest misunderstanding about property taxes and the assessor’s role
11:25 How better communication can help taxpayers understand their assessments
15:03 What the assessor controls versus what schools, municipalities, and taxing bodies control
17:34 How technology, AI, photos, and better data can improve assessment accuracy
27:50 What investors should review before filing a property tax appeal
40:46 Economic development, building more housing, and expanding the tax base
Takeaways for Chicago Property Managers and Landlords
Review your property data before assuming your assessment is correct.
The assessor does not control the entire tax bill, but the office plays a major role in valuation and predictability.
Cook County’s assessment system is more complicated than many other parts of Illinois.
Better data can lead to fairer assessments.
Condition matters. Two similar buildings on the same block may have very different values if one is renovated and one is not.
Property tax predictability is critical for underwriting and investment decisions.
Building more housing and commercial property can expand the tax base.
Expanding the tax base can help reduce pressure on individual property owners.
Investors should understand the appeal process, but the system should be easier for regular taxpayers to navigate.
Pat’s main goal is to reduce volatility and bring more transparency to the assessment process.
Guest info
Guest Name: Pat Hynes
Guest Company: Cook County
Guest Link: https://www.assessorhynes.com/
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
