THE CHICAGO COMMERCIAL REAL ESTATE FIELD GUIDEAn educational publication backed by Jaken Finance Group
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The Deal Lab.

Hypothetical commercial transactions, modeled from the investment thesis through cash flow, financing, downside risk and exit.

All scenarios are original hypothetical illustrations, not actual transactions or claimed Jaken-funded deals.
Deal Lab7 min read

Adaptive-reuse feasibility investment analysis

A conversion thesis needs a feasible new use, complete delivered cost, funded transition, supportable income, and an exit that compensates for execution risk.

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Deal Lab7 min read

Apartment refinance after a tax and insurance increase

A multifamily refinance must resize debt against higher recurring costs and reconcile the owner cash call with existing opportunity equity and future returns.

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Deal Lab7 min read

Commercial refinance shortfall and negotiated exit

A refinance gap requires a forward comparison of new cash, existing net sale equity, loan repayment, operating risk, and an executable negotiated or sale alternative.

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Deal Lab7 min read

Courtyard-building operating turnaround

A courtyard-building turnaround should improve collectible revenue and controllable operations without hiding maintenance, legal obligations, or capital behind a higher NOI target.

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Deal Lab7 min read

Hotel renovation and stabilization investment analysis

A hotel renovation must translate rooms and rates into property cash after operating costs, management obligations, reserves, renovation disruption, and debt.

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Deal Lab8 min read

Industrial property with an environmental diligence issue

A hypothetical industrial acquisition makes environmental uncertainty a priced condition, a funding and timing stress, and a lender/exit question rather than a generic contingency.

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Deal Lab7 min read

Medical-office property with tenant concentration

A hypothetical medical-office acquisition tests a major tenant’s credit and specialized space against vacancy, reuse capital, financing maturity, and a five-year exit.

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Deal Lab7 min read

Mixed-use property with a vacant commercial floor

A hypothetical mixed-use acquisition shows why occupied apartments cannot justify inserting vacant-floor market rent into current NOI without delivery capital, downtime, and financing.

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Deal Lab8 min read

Multifamily hold-versus-sell investment decision

A hold-versus-sell decision compares future cash from current net liquidation equity and new capital, rather than anchoring on historical purchase price or gross value.

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Deal Lab10 min read

Neighborhood shopping-center acquisition with CAM leakage

A hypothetical shopping-center acquisition shows how lease exclusions, capped recoveries, leasing capital, and debt service change the price an investor can justify.

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Deal Lab7 min read

Office acquisition with tenant improvements and leasing commissions

A hypothetical office acquisition exposes the cash cost of a major expiration: downtime, improvements, commissions, payment timing, and lower refinance capacity.

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Deal Lab7 min read

Owner-user industrial purchase comparing financing structures

An owner-user purchase must reconcile the real estate entity and operating business without counting internal rent twice, while preserving capital for both.

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Deal Lab7 min read

Restaurant property requiring substantial landlord improvements

A hypothetical restaurant-property acquisition separates landlord systems, tenant delivery funding, opening delays, and the credit risk behind an attractive rent.

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Deal Lab7 min read

Retail center exposed to an anchor co-tenancy clause

A hypothetical anchor departure reduces both direct rent and other tenants’ contractual payments, creating a correlated retail downside and a reserve funding test.

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Deal Lab7 min read

Self-storage expansion investment analysis

An existing self-storage property's expansion earns its return only after all-in construction costs, leasing friction, operating expenses, and transition liquidity reconcile.

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Deal Lab8 min read

Single-tenant NNN property with a near-term lease expiration

A hypothetical net-lease acquisition shows how a near-term expiry changes leasing capital, reserve consumption, loan maturity, and five-year equity returns.

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Deal Lab7 min read

Six-flat acquisition with deferred maintenance

A six-flat acquisition should fund existing defects and operating transition before evaluating recurring cash yield and a fully costed sale.

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Deal Lab7 min read

Small-bay industrial acquisition and lease-up

A hypothetical small-bay industrial acquisition connects divisible space, tenant demand, utility delivery, leasing costs, and the cash needed during incremental occupancy.

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Deal Lab7 min read

Storefront-plus-apartments acquisition

A hypothetical six-apartment and storefront acquisition separates commercial and residential collections, shared expenses, capital, financing, and the full equity return.

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Deal Lab8 min read

Warehouse with obsolete loading and clear height

A hypothetical older warehouse shows why a low price per square foot must be tested against tenant function, noncurable limitations, improvement cost, and exit liquidity.

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