One of our agents walked into a neighborhood estate sale and found a Victorian four-flat that the owner planned to sell himself, with three units still under construction. Every sale has to clear pricing, zoning, permits, appraisals, financing and negotiation before it can close, and finding a buyer covers only the first step. We walk through the FSBO risks Chicago sellers tend to miss and how a listing agent handles them before you go under contract.

While many buyers wait for the spring thaw to begin their home search, military families can gain a significant tactical advantage by buying in the winter. Reduced competition and highly motivated sellers provide a unique window for VA buyers to negotiate better prices and repair concessions. As the only Mil-Estate affiliate in Chicagoland, our veteran-led team helps you navigate these early-year opportunities to ensure a stress-free transition.

In today’s market, even good deals can fall apart if small issues go unchecked. Here are six of the most common deal killers we’ve seen 2025 and how buyers, sellers, and agents can stay prepared, avoid surprises, and keep transactions moving to the closing table.