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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

In today’s Chicago market, competition is fierce. Buyers are offering over asking, deals move in hours, and multiple bids have become the norm. So how can investors, rehabbers, or even first-time buyers stand out when price isn’t the only factor?

In this episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross break down actionable ways to make your offer more attractive, even when you can’t raise your price. From flexible terms to strategic communication, they share the real-world tactics that have helped them win deals in a crowded market.

Mark and Tom discuss the real-life negotiation levers that make sellers take notice. They go beyond the obvious “offer more money” and focus on everything else that influences a seller’s decision, speed, certainty, flexibility, and trust.

They explain how to use creative terms like leasebacks, waived contingencies, and strong earnest money to make your offer irresistible, even when others bid higher. You’ll also learn how to communicate effectively with brokers and sellers, when to take calculated risks like waiving inspections, and why networking and credibility matter as much as the numbers on your contract.

This episode is packed with insider insights from two experienced investors who have closed hundreds of deals in one of the toughest markets in the country.

Questions We Answer in This Episode

Q: What’s the first thing you can adjust when you can’t move on price?
A: Closing date. Offering a quick close can make you stand out, especially when competing buyers need 45 days. Even if it’s not always realistic (because of attorney review and title requirements), it looks appealing to most sellers and agents.

Q: What about when a seller needs more time?
A: Offer a leaseback. Many sellers, especially older owners moving to condos or estates, need the sale proceeds to buy their next home. Letting them stay for 60–90 days after closing, with rent or a security holdback, gives them flexibility and builds trust.

Q: Is waiving inspections ever a good idea?
A: It depends on your confidence and experience level. Chicago’s new 8.0 contract offers three inspection options:

Waive completely
Inspection with no right to request repairs
Inspection with right to request repairs
Waiving or limiting inspections can make your offer far more competitive, but only if you’ve done due diligence and understand the property’s condition.

Q: What are the biggest risks when waiving inspections?
A: Zoning surprises (like FAR limits or non-conforming layouts) and hidden repair costs. If you’re not doing a full gut rehab, a missed issue could turn a $200,000 renovation into $300,000.

Q: Should you worry about radon or sewer issues?
A: Not always. As Mark explains, many vacant properties have sewer problems that develop after sitting for years. It’s often a cost of doing business, something to fix before resale rather than during acquisition.

Q: How much earnest money should you put down?
A: More than you think. Illinois is very buyer-friendly, which means earnest money is often refundable. A “silly” amount of earnest money can make your offer look serious, even though it’s protected during attorney review.

Q: What does it mean to make earnest money “hard”?
A: It means your deposit becomes non-refundable from day one. It’s risky, but powerful. When you’re confident in a deal, hard earnest money can win against higher offers by showing total commitment.

Q: What about financing contingencies?
A: If you’ve closed with a lender before, consider waiving your financing contingency. It tells the seller you’ll close no matter what, even if your lender delays. That confidence gives you a major edge over standard financed buyers.

Q: Can being a licensed agent help?
A: Yes. Waiving your right to commission (or allowing the listing agent to double-end the deal) can make your offer cleaner and more appealing, especially now that commission structures are easier to negotiate post-NAR rule changes.

Q: How else can you stand out in a tie situation?
A: Relationships. Sellers and brokers prefer working with people they know and trust. Building a reputation for smooth closings and ethical behavior pays off when competition is tight.

Show Notes

00:00 Intro – Why deals are harder to win today
00:20 Setting the stage: competitive offers and limited inventory
01:13 Creative offer levers beyond price
01:45 Closing date strategy and “quick close” psychology
02:40 Leasebacks and why they build seller trust
03:39 How timing and seasons affect deal strategy 04:10 Handling construction timelines and financing delays
04:34 Using leasebacks to your advantage during permit waits
05:00 Discussion on inspection options in the 8.0 contract
06:10 Risks of waiving inspection and zoning pitfalls
07:00 Sewer and radon considerations for rehabbers
08:04 Earnest money strategy and Illinois contract flexibility
09:00 Going hard with earnest money, when and why
10:12 How to use hard money deadlines to negotiate extensions
10:44 Waiving financing contingencies to build confidence
11:27 Leveraging agent commissions as a negotiation tool
12:33 Why waiving commission gives you leverage
13:33 Importance of experienced brokers and attorney networks
14:25 How relationships and referrals build trust with sellers
15:23 Reputation, referrals, and proving your track record
15:56 Why repeat transactions make you the preferred buyer
16:19 Chicago Fact Trivia – “Name seven ‘S’ streets in Chicago!”

Takeaways for Chicago Property Managers and Landlords

Winning isn’t always about price. Terms and trust matter just as much.
Speed kills (in a good way). Quick closes grab attention, but so do leasebacks.
Earnest money speaks volumes. Even refundable deposits can look serious.
Waiving contingencies can be smart, when you understand the risk.
Relationships close deals. Brokers, attorneys, and repeat partners make transactions smoother.
Clarity wins. A simple, clean offer always beats one filled with conditions.

Guest Information

Guest Names: Mark Ainley & Tom Shallcross
Guest Company: Straight Up Chicago Investor Podcast
Guest Link: https://straightupchicagoinvestor.com

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Dear Investor,

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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.

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