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First-Time NNN Buyers Guide

Navigating Triple Net Lease Risks and Passive Real Estate Investment Challenges

By Thomas Wall, Partner at Anchor1031Updated September 25, 2025

Key Takeaway

NNN properties are NOT as passive as they're marketed to be. Despite broker claims of "set it and forget it" investing, direct NNN ownership requires active lease management, tenant oversight, and significant re-tenanting costs (5-15% of property value). For truly passive NNN exposure, Delaware Statutory Trust (DST) structures provide professional management and institutional-quality assets without the hands-on requirements of direct ownership.

Why are NNN properties so popular, and what risks do first-time buyers overlook? Over the past decade, triple-net or NNN properties have become increasingly popular with retail investors seeking to escape active property management. Brokers tout these investments as completely passive, where tenants handle all expenses while owners collect predictable rent. However, the reality is far more complex. For investors considering 1031 exchanges into NNN properties, understanding these risks is crucial before making investment decisions. This guide provides the framework for evaluating potential passive investment options and recognizing when Delaware Statutory Trust alternatives might provide better solutions.

The Surge in Triple Net Popularity

Perceived Passive Income

Tenants handle taxes, insurance, and maintenance - or so the marketing says

Predictable Cash Flow

Long-term leases (5-15 years) provide income visibility

"Anchor" Investment

Seen as stable, bond-like investments in portfolios

Escape Active Management

Perfect for investors tired of the "3 T's" - tenants, toilets, trash

Why NNNs Appeal to Investors

The appeal of triple net properties lies in their seemingly passive structure and predictable income. In a triple net lease, the tenant is responsible for maintenance costs, insurance, and property taxes. On the surface, this means investors don't have to worry about the usual headaches of property management and they know how much their income is going to be.

Additionally, many consider triple net properties to be an "anchor-type" asset. Simply put, these properties are seen as stable investments. When expenses and rents in the real estate market fluctuate, triple net properties theoretically pass on these costs to the tenant which maintains predictable income to the owner for the duration of the lease. This makes them particularly attractive for conservative investors entering retirement.

In my experience, 1031 exchange buyers are especially drawn to triple net properties. These buyers are usually looking to get out of active property management: the dreaded 3 T's of real estate: tenants, toilets, and trash. Investors, after having owned and operated their own rentals for decades, enter the marketplace looking for something passive.

However, investing in NNN properties is not as straightforward as it may seem. Investors need to understand the context and nuance of NNNs that their broker might not bring up when evaluating potential passive investment options. This article is intended to provide you with a framework for evaluating potential passive 1031 options and equip you with some key questions to ask about a potential investment property.

The Reality: NNN Properties Are Not Always Passive

Triple net investments are often marketed as passive—but that doesn't mean they're "set it and forget it." Issues do arise. A tenant might delay paying taxes or insurance premiums, leaving the landlord liable. In other cases, the tenant may vacate unexpectedly or return a property in poor condition despite lease obligations. Enforcing lease provisions often requires litigation, which is expensive and time-consuming. For a first-time buyer, this can feel overwhelming.

Common "Passive" Misconceptions:

  • Lease Enforcement: Landlords must actively monitor and enforce lease terms
  • Property Inspections: Regular oversight required to ensure tenant compliance
  • Lease Renewals: Complex negotiations critical for maintaining property value
  • Tenant Defaults: Landlords bear financial burden during tenant failures
  • Legal Issues: Evictions and lease disputes require active management

This is why investing in Delaware Statutory Trust properties with triple net lease assets can be a better option for most investors. DST investment properties allow you to access all the benefits of triple net lease properties—stable income, tenant-paid expenses, and inflation protection—without any of the hands-on management requirements. Professional asset managers handle tenant relations, lease negotiations, and property oversight, delivering the truly passive investment experience that many investors seek.

Comprehensive Risk Guide for First-Time NNN Buyers

Understanding these risks before investing can save you from costly mistakes and help you make informed decisions about NNN properties versus alternative investment structures.

Tenant Credit Risk

HIGH

Not all corporate leases are guaranteed by the parent company. Subsidiaries and franchisees can fail.

Overpaying for Yield

HIGH

Low cap rates for 'safety' can lock in poor risk-adjusted returns when disruption occurs.

Re-tenanting Costs

HIGH

Tenant improvements ($10-100/sq ft), broker fees (4-6%), and vacancy costs can equal 5-15% of property value.

Concentration Risk

CRITICAL

100% income from one tenant, one location, one lease. Total cash flow loss if tenant leaves.

Market & Location Risk

HIGH

Tertiary markets and hard-to-access locations make re-tenanting extremely difficult.

Liquidity & Exit Timing

MEDIUM

Property value declines as lease burns off. Forced sales without strong tenants mean significant losses.

Lease Complexity

MEDIUM

Not all 'triple nets' are the same. Early termination clauses and cost shifts can blindside new buyers.

Bank Restrictions

MEDIUM

Lenders control tenant replacement and can restrict renegotiation flexibility when you need it most.

Inflation Risk

MEDIUM

Fixed rent schedules or minimal escalations (1% annually) erode purchasing power over 15-year terms.

Deferred Maintenance

MEDIUM

Landlords inherit significant repair costs when leases end - roofs, parking, HVAC past useful life.

Real-World Case Study: Catherine's Dollar General Experience

Catherine's Story: From Steady Income to Forced Sale

A real example of how location risk can devastate NNN investments

The Setup

Catherine inherited management of several NNN properties after her husband passed away. One property was a Dollar General in a rural town that had reliably paid rent for nearly a decade with minimal input. She estimated the property was worth about $1,200,000.

The Problem

Dollar General opened a new store in the town up the road and vacated Catherine's building. Despite having 2 years remaining on the lease and continuing to pay rent (going "dark"), the rural location made re-tenanting impossible.

The Outcome

Even with a 2-year runway to find a new tenant, Catherine couldn't sign a new lease due to the rural location. The carrying costs became too great, and she was forced to sell the vacant building for only $400,000 - a 67% loss from her estimated value.

The Solution

After this experience, Catherine sold her remaining commercial properties while they still had tenants and completed 1031 exchanges into a diversified portfolio of DSTs. She traded slightly higher cap-rates for professional management and diversification.

The team at Anchor1031 has seen many variations of this story over the years. Even if DSTs are not right for you, and you plan on stepping into the NNN world as a means of going passive, please use this guide as you conduct due diligence on potential investments. Understanding the nuances of 1031 exchange rules and recognizing potential investment risks is crucial for making informed decisions.

Delaware Statutory Trust: The Superior NNN Alternative

For investors seeking truly passive exposure to NNN properties, Delaware Statutory Trust structures offer potential advantages over direct ownership. DSTs provide access to institutional-quality NNN assets with professional management, eliminating the hands-on requirements that make direct NNN ownership challenging.

Why DST NNN Properties Provide Better Passive Exposure

  • Professional Management: Experienced asset managers handle all lease negotiations, tenant relations, property inspections, and legal issues without investor involvement.
  • Diversification Benefits: Many NNN DSTs include multiple properties across different markets and tenants, reducing single-asset concentration risk.
  • Institutional Quality: DST sponsors typically acquire higher-quality assets in better locations with stronger tenants than individual investors can access.
  • No Re-tenanting Risk: Professional sponsors handle all aspects of lease renewals and re-tenanting, eliminating the 5-15% cost burden from investors.
  • Legal Expertise: Professional legal teams handle all lease complexities, ensuring optimal terms and protecting investor interests.

Key Advantages for 1031 Exchange Investors

DST structures are specifically designed for 1031 exchanges, providing seamless tax deferral opportunities while delivering true passive income. For investors concerned about timing pressures, our guide on 1031 backup strategies explains how DSTs can serve as contingency options when direct property acquisitions become challenging.

Additionally, DSTs can help investors avoid paying boot taxes by precisely matching exchange values, something that's often difficult with individual NNN properties. Understanding debt risks in real estate is also important when evaluating leveraged NNN investments.

NNN Investment Strategy Summary:

  • Direct Ownership Reality: Requires active management despite marketing claims of passivity
  • Major Risks: Concentration risk, re-tenanting costs, tenant credit issues, location challenges
  • DST Advantage: Truly passive exposure with professional management and diversification
  • Strategic Focus: Better locations, stronger tenants, institutional-quality assets

Considering NNN Properties for Your 1031 Exchange?

Learn how Delaware Statutory Trust NNN properties can provide truly passive exposure without the risks and management requirements of direct ownership.

Schedule Your Strategy Call

Making Informed NNN Investment Decisions

Triple net properties can indeed be a great fit for certain investors, especially those seeking stability and predictable income. But they are not without risks and might not suit every investor seeking passive income. For first-time buyers, the key is to move cautiously: scrutinize the tenant's true credit, evaluate the location as if it were vacant, understand every nuance of the lease, and plan for what happens when the current lease ends.

In other words, treat NNN as an investment with both upside and downside. They are not a bond substitute. The marketing of "mailbox money" and "passive income" can be misleading when the reality involves active lease management, tenant oversight, and significant re-tenanting costs.

For professional guidance in navigating these complexities and exploring alternative passive investment strategies through Delaware Statutory Trust structures, consider consulting with a representative at Anchor1031. Our approach prioritizes risk assessment and education, ensuring you understand both the potential rewards and inherent challenges of any investment strategy.

Before Investing in Direct NNN Properties, Consider:

  • • Can you handle active lease management and tenant relations?
  • • Do you have reserves for re-tenanting costs (5-15% of property value)?
  • • Is the location viable for alternative tenants if current tenant leaves?
  • • Have you analyzed the lease with experienced legal counsel?
  • • Would DST NNN properties provide better passive exposure for your situation?

Remember, there are no guarantees in real estate, but with comprehensive education and expert guidance, you can make more confident decisions about what type of asset is right for your investment strategy. Whether you choose direct NNN ownership or DST alternatives, understanding the full spectrum of risks and opportunities is essential for successful passive real estate investing.

Important 1031 Exchange Reminder

If you're considering a 1031 exchange into NNN properties, remember that you must work with a qualified intermediary to ensure IRS compliance. A qualified intermediary facilitates the exchange process, holds your proceeds, and ensures all timing requirements are met. Learn more about the 7 essential IRS rules every investor must follow.

Need help finding a qualified intermediary? Our team at Anchor1031 can provide referrals to qualified intermediaries we have worked with for many years and can confidently recommend. We also have a guide on 6 essential questions to ask when selecting your QI.

Frequently Asked Questions

Thomas Wall

About Thomas Wall

Thomas Wall has nearly a decade of experience in alternative investments and real estate. He has helped financial advisors at banks and wirehouses navigate a broad spectrum of equity, debt, and retirement investments at AIG which contributed to over $200MM of capital invested. From there, Thomas specialized in helping real estate investors navigate the transition from active management to passive real estate investing. He advises high-net-worth investors on 1031 exchanges, DSTs, private real estate offerings, and REITs. He has helped investors through hundreds of 1031 exchanges, placing over $230MM of equity into real estate. Today, with Anchor1031, he focuses on providing his investors with the tools they need to accurately assess risk and successfully defer taxes when repositioning their real estate portfolio and making the transition from active manager to passive investor.

Partner, Anchor1031

Ready to Explore Truly Passive NNN Alternatives?

Now that you understand the reality of direct NNN ownership, let our team help you explore Delaware Statutory Trust NNN properties that provide genuine passive exposure without the management requirements.

Continue your asset class education with our comprehensive guides:

Disclosure

Tax Complexity and Investment Risk

Tax laws and regulations, including but not limited to Internal Revenue Code Section 1031, bonus depreciation rules, cost segregation studies, and other tax strategies, contain complex concepts that may vary depending on individual circumstances. Tax consequences related to real estate investments, depreciation benefits, and other tax strategies discussed herein may vary significantly based on each investor's specific situation and current tax legislation. Anchor1031, LLC and Great Point Capital, LLC make no representation or warranty of any kind with respect to the tax consequences of your investment or that the IRS will not challenge any such treatment. You should consult with and rely on your own tax advisor about all tax aspects with respect to your particular circumstances. Please note that Anchor1031 and Great Point Capital, LLC do not provide tax advice.

Anchor1031

The information contained in this article is for general educational purposes only and does not constitute legal, tax, investment, or financial advice. This content is not a recommendation or offer to buy or sell securities. The content is provided as general information and should not be relied upon as a substitute for professional consultation with qualified legal, tax, or financial advisors.

Tax laws, regulations, and IRS guidance regarding 1031 exchanges are complex and subject to change. Information herein may include forward-looking statements, hypothetical information, calculations, or financial estimates that are inherently uncertain. Past performance is never indicative of future performance. The information presented may not reflect the most current legal developments, regulatory changes, or interpretations. Individual circumstances vary significantly, and strategies that may be appropriate for one investor may not be suitable for another.

All real estate investments, including 1031 exchanges, are speculative and involve substantial risk. There can be no assurance that any investor will not suffer significant losses, and a loss of part or all of the principal value may occur. Before making any investment decisions or implementing any 1031 exchange strategies, readers should consult with their own qualified legal, tax, and financial professionals who can provide advice tailored to their specific circumstances. Prospective investors should not proceed unless they can readily bear the consequences of potential losses.

While the author is a partner at Anchor1031, the views expressed are educational in nature and do not guarantee any particular outcome or create any obligations on behalf of the firm or author. Neither Anchor1031 nor the author assumes any liability for actions taken based on the information provided herein.