The Top 6 Deal Killers in 2025 and How to Keep Your Transaction on Track
Every deal that makes it to the closing table has one thing in common: persistence.
Whether it’s a first-time homebuyer trying to line up financing or a seasoned investor working through an inspection report, there’s always something that can throw a wrench into the process.
The housing market in 2025 is still tough. High rates and limited inventory keep pressure on both sides, but buyers, sellers, and agents have learned how to navigate it with more awareness and preparation than in past years.
Some issues come up again and again, and while a few are unavoidable, most can be managed with the right mix of communication, preparation, and patience. Below are six of the most common deal killers we’ve seen this year, along with practical ways to work through each one.
1. Low Appraisals (Especially on VA Loans)
Appraisals are meant to keep everyone honest about value, but they can be one of the most stressful parts of the process. Over the past few years, appraisers have been conservative, especially in neighborhoods where recent sales don’t match asking prices or where renovation quality varies from block to block.
For VA buyers, the scrutiny can be even higher. VA appraisers are required to follow strict guidelines and may call out repairs or safety issues that a conventional appraisal would pass without mention. This protects veterans, but it can also slow things down or create unexpected costs.
How to work around it:
Get ahead of the data. Pull recent comparable sales that truly support the price, not just the most flattering ones. Providing these details to the appraiser early can set realistic expectations.
Prepare for small gaps. If the appraisal comes in low, it doesn’t automatically end the deal. Buyers and sellers can often meet in the middle through price adjustments or closing cost credits.
Show your work. Sellers who document upgrades, repairs, and replacements give appraisers tangible evidence of value that might not show up in the data.
Being transparent early helps everyone avoid surprises later.
2. Sellers with Unrealistic Expectations
Every seller wants the best possible price, but pricing based on hope instead of data is one of the fastest ways to stall a sale. Some homeowners still reference the 2021 and 2022 boom when values climbed almost weekly. Today’s market moves slower. Buyers are more cautious, and homes that are priced correctly from day one tend to sell faster and closer to asking.
An unrealistic price not only limits buyer interest, it can also make a home feel stale after a few weeks. That often leads to reductions later, which usually end up lower than if the home had been priced realistically from the beginning.
How to work around it:
Lean on the numbers. Use recent neighborhood comps and pay attention to pending sales and days on market.
Be open to feedback. If showings are slow or feedback is consistent, adjust early rather than waiting.
Make it easy to like. Small, cost-effective improvements like paint, lighting, and repairs can help the home compete.
Stay objective. Emotional attachment is natural, but buyers compare square footage, finishes, and location, not memories.
The goal isn’t to win the pricing game. It’s to sell at fair market value, in a reasonable time, with minimal stress.
3. Missing or Incomplete Multifamily Documentation
Multifamily deals can be rewarding but are often fragile. Many small and mid-size landlords still keep minimal records, including handwritten rent rolls, missing receipts, or vague maintenance details, and that can make lenders nervous.
When a buyer’s underwriter can’t verify income and expenses, it can lead to delays, reappraisals, or even cancellations.
How to work around it:
For sellers: Start documenting early. Keep rent rolls, leases, expense records, and repair invoices organized.
For buyers: Ask for documentation upfront, not after your offer is accepted. Include rent rolls, leases, financial data, for the last 24-36 months, and service records in the initial request.
For both sides: Transparency helps everyone. A clear record of income and expenses supports a fair valuation and smoother financing.
When the numbers tell a clear story, lenders can focus on the property instead of playing detective.
4. Buyers Running Short on Closing Funds
This happens more often than people think. Buyers are pre-approved, they’ve done the math, and then something changes: insurance rates rise, the appraisal comes in low, or a rate lock expires. Suddenly, they’re short on funds at the closing table.
The past few years have also seen rising costs tied to HOA fees, escrow adjustments, and repairs. When buyers are already stretched thin, these changes can make it hard to close on time.
How to work around it:
Get a full loan estimate early. A detailed breakdown of taxes, insurance, and closing costs provides a more complete picture.
Use available programs. Many buyers qualify for state and local assistance, including IHDA, VA, and lender-based grants.
Negotiate smart credits. Seller credits or lender-paid buydowns can help cover shortfalls without changing the purchase price.
Keep reserves when possible. Even a small emergency cushion can make a big difference when last-minute costs appear.
Planning ahead and communicating with your lender at every step is the best safeguard against last-minute surprises.
5. Financing Delays and Underwriting Surprises
Even the most qualified buyers can run into unexpected issues once underwriting begins. A job change, new debt, or unverified gift funds can pause the process while the lender rechecks income and assets.
Post-pandemic verification standards are strict, and even small inconsistencies can trigger reviews. Most delays, however, are preventable.
How to work around it:
Keep finances steady. Avoid new credit, large deposits, or moving money between accounts mid-process.
Prepare documents early. Have pay stubs, bank statements, and verification letters ready.
Build flexibility into the contract. Include a short extension clause to prevent technical delays from derailing the deal.
Communicate often. Buyers, agents, and lenders should check in weekly to confirm progress.
Proactive communication beats last-minute scrambling every time.
6. Inspection Fallout
Inspections are designed to inform, not to end deals, but they’re often where negotiations break down. Chicago’s housing stock is older, and wear is expected, yet some buyers expect perfection while some sellers dismiss valid concerns. Both extremes can cause a transaction to fall apart.
How to work around it:
Set expectations early. Every property will have minor flaws. Focus on health, safety, and structural items.
Focus on major issues. Roofs, plumbing, electrical, and foundation systems should take priority.
For sellers: Fix simple items before listing. Easy fixes like replacing GFCI outlets or sealing gaps avoids red flags.
Keep emotions out of it. Inspection reports can be long, but most items are manageable. Look for solutions instead of placing blame.
A balanced, professional approach helps both sides reach the finish line with confidence.
Most deals don’t fall apart because of one big mistake. They unravel when small issues are ignored. The strongest transactions are built on communication, documentation, and realistic expectations from day one.
The truth is that most deal killers are really deal slowdowns. With the right prep and a team that knows how to problem-solve, almost any challenge can be overcome.
If you’re planning to buy, sell, or invest before the end of the year, keep these lessons in mind and work with professionals who know how to keep things moving. That’s where deals are saved and great results happen.
