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Chicago Property Management Insights

RESOURCES FOR OWNERS & INVESTORS

Blog Choosing a Local Property Management Company as an Out-of-State Investor

Choosing a Local Property Management Company as an Out-of-State Investor

By Jason Donajkowski - Thursday, August 21, 2025
We love it when investors come to the Chicago real estate market from out of state. We understand what a great city this is because we live here. We work here. We know that there are so many opportunities to earn great cash flow and a lot of long-term wealth when you choose the r...
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Blog Preparing Your Chicago Rental Property for Success: A Pre-Listing Checklist from Paragon

Preparing Your Chicago Rental Property for Success: A Pre-Listing Checklist from Paragon

By Jason Donajkowski - Thursday, July 17, 2025
Ready to rent out a property in Chicago?Before you start sharing a listing and offering showings, make sure that property is prepared. If it’s not move-in ready and attractive to well-qualified renters, you might find yourself facing a longer vacancy or settling for a ...
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Blog How the “One Big Beautiful Bill” Reignites Real Estate: What Smart Investors Should Do Now

How the “One Big Beautiful Bill” Reignites Real Estate: What Smart Investors Should Do Now

By Jason Donajkowski - Wednesday, July 9, 2025
Quietly tucked into the middle of summer, Congress passed the "One Big Beautiful Bill Act" (OBBBA 2025), and it's a game changer for small real estate investors.This legislation reopens powerful tax strategies that had been fading, reinforcing real estate’s pl...
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Blog From Headaches to Hands-Off: How Property Management Eliminates Maintenance Burdens for Chicago Landlords

From Headaches to Hands-Off: How Property Management Eliminates Maintenance Burdens for Chicago Land...

By Jason Donajkowski - Thursday, June 19, 2025
Have you been wondering how to manage your Chicago rental properties while you’re also trying to manage the rest of your life, like a career, a family, a set of passions and pursuits, not to mention a growing interest in real estate investments? If you want to be a lan...
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Blog The Chicago Landlord and Tenant Ordinance: A Comprehensive Guide for Property Owners

The Chicago Landlord and Tenant Ordinance: A Comprehensive Guide for Property Owners

By Jason Donajkowski - Thursday, May 15, 2025
How worried are you about making a legal mistake with your rental property?Most landlords do worry that they’re missing something. There are so many state, federal, and local laws to follow as an investor or landlord. This is part of navigating the world of rental prop...
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Blog What I Wish I Knew About Real Estate Investing Before I Started

What I Wish I Knew About Real Estate Investing Before I Started

By Jason Donajkowski - Tuesday, May 13, 2025
The Numbers Don’t Tell the Whole StoryWhen I first entered real estate investing, I believed the best opportunities came from properties with the highest projected returns on paper. The math looked great: low purchase price, high rent, strong cash flow. But over time—...
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Blog 5 Ways to Avoid Tenant Turnover and Keep Your Chicago Property Rented

5 Ways to Avoid Tenant Turnover and Keep Your Chicago Property Rented

By Jason Donajkowski - Thursday, April 17, 2025
Avoiding tenant turnover is an important strategy in any profitable investor’s action plan. You want to keep your good tenants in place because when they leave, you’re not only faced with a vacancy, you’re also left paying for turnover costs, general maintenance...
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Blog Important Questions Buyers and Sellers Should Ask in Today’s Real Estate Market

Important Questions Buyers and Sellers Should Ask in Today’s Real Estate Market

By Jason Donajkowski - Monday, April 14, 2025
In today’s evolving real estate market—shaped by higher interest rates, changing inventory levels, and shifting buyer demand—it’s more important than ever for buyers and sellers to approach the process thoughtfully and strategically. Whether you’re p...
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Blog The Shift Toward Income-Generating Real Estate: Why Investors Are Prioritizing Cash Flow Over Speculation

The Shift Toward Income-Generating Real Estate: Why Investors Are Prioritizing Cash Flow Over Specul...

By Jason Donajkowski - Thursday, April 10, 2025
In today's uncertain financial environment, there's a growing shift in global finance toward income-generating real estate. As traditional investment markets experience increased volatility and inflation continues to erode purchasing power, both individual investors and i...
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Blog Important Personality Traits to Look for in Your Next Chicago Real Estate Broker

Important Personality Traits to Look for in Your Next Chicago Real Estate Broker

By Jason Donajkowski - Tuesday, April 8, 2025
Choosing the right real estate broker can make a huge difference in your experience and outcome, whether you're buying, selling, or investing. While market knowledge and transactional experience are essential, equally important are the personality traits that determine how ef...
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