CRE Loan Workouts & Borrower-Side Restructuring

Our primary focus at Douglass Advisory is to develop a comprehensive, lender-ready business plan that evaluates every viable option for your property and your financial position.
We assess restructuring paths, stabilization strategies, cash-flow scenarios, and long-term asset plans—then determine which combination of solutions is most effective for your specific situation.
We package these findings into a professional, data-supported proposal that strengthens your negotiating position, clearly communicates the path forward, and helps lenders approve the most favorable workout structure possible.

Commercial real estate has entered one of the most complex financial cycles in
decades—shifting interest rates, softening asset values, lender pressure, maturing debt, and liquidity constraints.
At Douglass Advisory, we specialize exclusively in borrower-side workout strategies, helping owners preserve their assets, stabilize cash flow, and navigate lender negotiations from a position of strength.
Whether you are facing an upcoming maturity, covenant breach, cash-flow shortfall, or a special-servicer escalation, we provide clear direction, sophisticated financial modeling, and strong negotiation positioning to protect your investment.

Many borrowers are dealing with capital stacks that no longer reflect market realities. We help you restructure your debt in ways that create flexibility, reduce pressure, and extend your operational runway.

Our services include:
Interest-rate restructuring or repricing
Maturity extensions tied to performance targets
Amortization relief and payment restructuring
Refinancing analysis and lender-readiness preparation
Negotiation strategies to secure favorable terms

Our models show lenders a credible path to stabilization and recovery—dramatically improving leverage in negotiations.

Negotiating Extensions & Forbearance
We structure and lead the negotiation for:
Temporary forbearance to stabilize operations
Short- and long-term maturity extensions
Waivers for covenant compliance issues
DSCR relief agreements
Modified reserve and TI/LC funding requirements
We present a lender-grade narrative supported by data, making it easier for financial institutions to approve borrower-friendly solutions.

When the property itself must evolve, we help craft a repositioning strategy that
strengthens the asset and reassures lenders.

This may include:
Operational resets to improve NOI
Lease-up strategy and absorption modeling
Market-driven repositioning of use/class
Adaptive reuse analysis

Capital improvement ROI modeling
Stabilization timelines tied to lender concessions
We translate these into clear financial projections that build lender confidence and strengthen your negotiating position.

Borrowers who present strong financial analysis win better outcomes.
We build:
3–10 year cash-flow models
DSCR/NOI/IRR sensitivity scenarios
Stress-testing across rate and occupancy changes
Base-case, downside, and recovery scenarios
Capital, lease-up and operating cost forecasts
These models demonstrate your ability to recover value and justify lender cooperation.

When the capital structure itself must change, we advise on:
Mezzanine debt restructuring
Preferred equity solutions
Rescue capital
Intercreditor complexity
Subordinated capital negotiations
Waterfall redesign for complex ownership groups
We help balance your obligations while protecting equity value and maintaining operational control.

If a sale is the optimal path, we advise borrowers on how to:
Evaluate market timing and valuation windows
Structure sales that minimize losses
Present lenders with a coordinated exit strategy
Prepare financial documentation for buyers
Coordinate with brokers, attorneys, and lenders for approval
Our goal is to protect as much borrower equity as possible while ensuring a clean, lender-approved exit.

Whether you’re facing DSCR shortfalls, occupancy drops, reserve depletions, or financial reporting breaches, we help you get ahead of the issue and present solutions to lenders before they escalate.

We analyze:
Severity of breach
Financial exposure
Cure options
Negotiation leverage
Documentation requirements
Impact on future refinance or sale
Proactive communication greatly reduces the risk of enforcement actions.

Special servicers are sophisticated and process-driven—borrowers must be equally prepared.
We help borrowers:
Understand the special servicer’s incentives

Present credible stabilization plans
Prepare valuation, cash-flow, and recovery models
Avoid unnecessary transfers to foreclosure counsel
Negotiate modifications, and extensions
Manage reporting and documentation
We position you for the most constructive modification possible.

If fresh capital is required, we help design and evaluate:
Preferred equity injections
Rescue capital structures
Joint-venture recaps
Equity dilution vs. preservation models
Waterfall reformations for incoming capital
Our goal is to secure capital that protects your long-term equity value while restoring lender confidence.

CRE loan workouts often require legal coordination, especially when dealing with special servicers, covenant breaches, intercreditor agreements, or restructuring documents. We work seamlessly with your existing attorney to ensure a unified approach—combining legal protection with financial and operational strategy.

If you do not currently have counsel, we can help you identify and engage an experienced real estate attorney who specializes in workouts, restructuring, and lender negotiations. We ensure all parties work in alignment to protect your property, your equity, and your long- term interests.