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William Rapp, based in Houston, TX, US, is currently a Capital Advisor at Medallion Funds, bringing experience from previous roles at eXp Commercial, NEXA Mortgage, Viking Enterprise LLC and Sun Realty - Houston. William Rapp holds a 1997 - 2001 BBA in Finance @ Texas A&M University. With a robust skill set that includes REO, Sellers, SFR, FHA financing, Reverse Mortgages and more, William Rapp contributes valuable insights to the industry.

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šŸ¢ Top Commercial Real Estate Lending Mistakes Investors Make Before Closing āš ļø

šŸ’° Common Lending Mistakes CRE Investors Make (and How to Avoid Costly Financing Errors) 🚫

December 22, 2025•3 min read

šŸ’° Common Lending Mistakes CRE Investors Make (and How to Avoid Costly Financing Errors) 🚫

šŸ¢ Top Commercial Real Estate Lending Mistakes Investors Make Before Closing āš ļø


Common Lending Mistakes CRE Investors Make

Commercial real estate financing is rarely simple—and small mistakes at the loan-structuring stage can cost investors hundreds of thousands of dollars over the life of a deal. From choosing the wrong loan product to misunderstanding lender underwriting priorities, these errors often surface late in the process when options are limited.

As a mortgage broker working across banks, agencies, CMBS lenders, and private capital, I see the same lending mistakes repeated again and again. Below are the most common commercial real estate lending mistakes—and how smart investors avoid them.


1. Choosing the Loan Based on Rate Alone

Interest rate is only one component of a commercial loan—and often not the most important.

Common issues include:

  • Ignoring prepayment penalties (yield maintenance or defeasance)

  • Overlooking recourse exposure

  • Selecting short-term debt for long-term assets

  • Missing flexibility for future refinances or sales

A slightly higher rate with better terms often produces a stronger long-term outcome.


2. Not Matching the Loan Structure to the Business Plan

A value-add deal, stabilized property, and owner-occupied acquisition all require different financing strategies.

Mistakes occur when investors:

  • Use permanent debt for transitional assets

  • Use bridge debt without a clear exit

  • Underestimate seasoning requirements for take-out financing

Your financing should support your timeline, risk tolerance, and exit strategy, not work against it.


3. Underestimating DSCR and Cash Flow Requirements

Many investors focus on purchase price and loan-to-value while overlooking debt service coverage ratio (DSCR).

Lenders care about:

  • Net operating income sustainability

  • Stress-tested cash flow

  • Market vacancy assumptions

Over-leveraging a deal often leads to reduced proceeds, higher pricing, or a declined loan late in underwriting.


4. Poor Financial Documentation Preparation

Incomplete or inconsistent documentation slows deals and weakens borrower credibility.

Common mistakes:

  • Outdated or mismatched rent rolls and P&Ls

  • Missing entity documents

  • Unexplained income or expense anomalies

  • Weak personal financial statements for guarantors

Well-prepared financials signal professionalism and reduce lender friction.


5. Ignoring Recourse and Guarantee Language

Not all ā€œnon-recourseā€ loans are truly non-recourse.

Investors are often surprised by:

  • Bad-boy carveouts

  • Environmental or fraud triggers

  • Partial or burn-off recourse structures

Understanding guarantee exposure before signing a term sheet is critical to risk management.


6. Waiting Too Long to Involve a Mortgage Broker

Many investors approach lenders directly without understanding how capital markets price risk.

A mortgage broker:

  • Shops multiple lenders simultaneously

  • Structures leverage and terms strategically

  • Anticipates underwriting objections early

  • Aligns the loan with future refinancing options

Early involvement creates leverage—not cost.


7. Assuming All Lenders Underwrite the Same Way

Banks, agencies, CMBS lenders, and debt funds each evaluate risk differently.

Differences include:

  • How income is calculated

  • Treatment of tenant rollover

  • Market concentration limits

  • Appetite for specialized assets

Understanding lender psychology is just as important as understanding the numbers.


Final Takeaway

Commercial real estate lending mistakes are rarely fatal—but they are expensive.

The best investors treat financing as a strategic tool, not a commodity. Proper loan structuring preserves equity, improves returns, and protects flexibility in changing markets.

If you are buying, refinancing, or repositioning a commercial property, the right financing strategy can be the difference between a good deal and a great one.


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Ā© 2023-2024 Bill Rapp, Medallion Funds LLC, Director of Capital Advisory


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Bill Rapp - Commercial & Residential Mortgage Broker

Whether you're a first-time homebuyer, a seasoned investor, or a business owner with ambitious plans, securing the right financing is crucial. At Medallion Funds, we take the guesswork out of mortgages, offering a comprehensive suite of residential and commercial loan options to fit your unique needs. Looking for Your Dream Home? We understand the excitement and challenges of navigating the residential real estate market. Our experienced mortgage brokers will guide you through every step, from pre-qualification to closing. We offer a variety of loan programs to suit your financial situation, including: • Fixed-rate mortgages: Offering stability with predictable monthly payments. • Adjustable-rate mortgages (ARMs): Providing competitive rates for a set period. • FHA loans: Making homeownership accessible with lower down payments. • VA loans: Rewarding veterans with attractive rates and flexible terms. Investing in Your Business Future? Growth often requires capital, and we can help you unlock the potential of your commercial property. Our brokers specialize in a wide range of commercial loan options, including: • Purchase loans: Financing the acquisition of new buildings or land. • Construction loans: Facilitating the development of your project. • Refinance loans: Restructuring your existing mortgage for better terms. • SBA loans: Providing access to government-backed financing for qualified businesses. The Medallion Funds Difference: We go beyond simply finding a loan. We take the time to understand your goals and develop a personalized strategy. Here's what sets us apart: • Expertise: Our brokers have a deep understanding of both residential and commercial lending. • Competitive Rates: We leverage our strong lender relationships to secure the best possible terms. • Streamlined Process: We handle the paperwork, keeping you informed every step of the way. • Exceptional Service: We're committed to providing you with a positive and stress-free experience. Ready to Take the First Step? Contact Medallion Funds today for a free consultation. Let's discuss your financing needs and help you achieve your dreams!

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Corporate NMLS NMLS # 1825831 | Company Website: https://medallionfunds.com/bill-rapp/

Copyright ©2021 | Mortgage Viking Team Licensed to Do Business | NMLS # 228246

This is not an offer to enter into an agreement. Not all customers will qualify. Information, rates and programs are subject to change without notice. All products are subject to credit and property approval. Other restrictions and limitations may apply

Corporate | NMLS ID NMLS # 1825831

Corporate Address : 2651 N. Green Valley Pkwy STE. 101 Henderson, NV 89014 https://medallionfunds.com/bill-rapp/