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Chapter 11-The Registered Investment Advisor Perspective ~ The Strategic 1031 Exchange-Executive Reference Guide

Al DiNicola

Build­ing the portfolio—not sim­ply replac­ing a prop­er­ty

By Al DiNi­co­la, AIF®

Pri­vate Mar­kets / 1031 Exchange / DST Com­men­tary
DST 1031 Spe­cial­ist
Fidu­cia­ry Cap­i­tal Man­age­ment, LLC
Secu­ri­ties offered through MSC-BD, LLC, Mem­ber of FINRA/SIPC

Reg­is­tered Invest­ment Advi­sors are often asso­ci­at­ed with pub­lic-mar­ket port­fo­lios, finan­cial plan­ning, retire­ment pro­jec­tions, and ongo­ing wealth man­age­ment. Yet for many afflu­ent investors, real estate rep­re­sents one of the largest com­po­nents of net worth.

A client may own:

In some cas­es, the val­ue of the client’s real estate hold­ings may sub­stan­tial­ly exceed the val­ue of the client’s bro­ker­age accounts, retire­ment plans, and liq­uid invest­ments com­bined. This cre­ates an impor­tant role for the RIA (SEC, Com­mis­sion Inter­pre­ta­tion Regard­ing Stan­dard of Con­duct for Invest­ment Advis­ers, 2019). The RIA should not view a Sec­tion §1031 exchange as a tax trans­ac­tion occur­ring out­side the port­fo­lio. It is a major cap­i­tal-allo­ca­tion event. The sale of an appre­ci­at­ed prop­er­ty may release mil­lions of dol­lars of equi­ty and cre­ate a rare oppor­tu­ni­ty to recon­sid­er:

The replace­ment-prop­er­ty deci­sion should there­fore be inte­grat­ed into the investor’s over­all wealth plan. The cen­tral ques­tion is not mere­ly:

“Which replace­ment prop­er­ty should the client acquire?”

It is:

“How should the client’s total cap­i­tal be allo­cat­ed across real estate, pub­lic secu­ri­ties, pri­vate invest­ments, cash, debt, and estate-plan­ning struc­tures to max­i­mize long-term after-tax wealth?” This is the RIA per­spec­tive with­in After-Tax Wealth Opti­miza­tion™.

Real Estate Is Part of the Portfolio

Real estate investors often think of their prop­er­ty hold­ings sep­a­rate­ly from their invest­ment port­fo­lios.

They may refer to:

“My real estate.”

“My stocks.”

“My retire­ment accounts.”

“My cash.”

“My busi­ness.”

From an eco­nom­ic per­spec­tive, how­ev­er, all of these assets are part of one bal­ance sheet. Each asset con­tributes to the client’s:

A client with $10 mil­lion in com­mer­cial real estate and $2 mil­lion in mar­ketable secu­ri­ties does not have a bal­anced $12 mil­lion port­fo­lio mere­ly because the secu­ri­ties account con­tains mul­ti­ple mutu­al funds. The client may still be over­whelm­ing­ly con­cen­trat­ed in real estate. The RIA can help the client under­stand total port­fo­lio expo­sure rather than eval­u­at­ing only the por­tion held in a man­aged account. This requires a com­pre­hen­sive bal­ance-sheet approach.

Portfolio Construction

Port­fo­lio con­struc­tion is the process of com­bin­ing assets in a way that sup­ports the investor’s objec­tives while man­ag­ing risk. The start­ing point should not be a prod­uct.

It should be the client.

A thought­ful port­fo­lio-con­struc­tion process con­sid­ers:

The RIA should deter­mine what role each asset is expect­ed to per­form.

For exam­ple:

Direct real estate may pro­vide income, appre­ci­a­tion, and tax ben­e­fits. DSTs may pro­vide pas­sive real estate expo­sure and poten­tial §1031 replace­ment-prop­er­ty treat­ment. Pri­vate funds may pro­vide spe­cial­ized alter­na­tive expo­sure. Insur­ance may pro­vide risk trans­fer or estate liq­uid­i­ty. Trust struc­tures may sup­port suc­ces­sion and wealth trans­fer. The goal is not to own every avail­able asset class. The goal is to cre­ate a coher­ent port­fo­lio in which each allo­ca­tion serves a pur­pose.

Every Dol­lar Has a Job

A use­ful cap­i­tal-allo­ca­tion frame­work begins by assign­ing each dol­lar a func­tion. Cap­i­tal may be intend­ed to pro­vide:

Prob­lems arise when one invest­ment is expect­ed to serve every objec­tive. A sin­gle replace­ment prop­er­ty may be asked to pro­vide:

No invest­ment can max­i­mize all of these char­ac­ter­is­tics at the same time. The RIA can help the client sep­a­rate objec­tives and allo­cate cap­i­tal accord­ing­ly. For exam­ple, the client may use:

Risk-Adjusted Returns

Investors often focus on pro­ject­ed return with­out ful­ly eval­u­at­ing the amount of risk required to achieve it. A 9% pro­ject­ed return is not auto­mat­i­cal­ly supe­ri­or to a 7% pro­ject­ed return. The 9% return may depend upon:

“Which invest­ment offers the high­est pro­ject­ed return?”

It is:

“Which invest­ment offers the most appro­pri­ate expect­ed return for the risks the client is accept­ing?”

Understanding the Sources of Return

Real estate returns may come from sev­er­al sources:

Cur­rent rent col­lect­ed under a strong lease may be more pre­dictable than a pro­ject­ed sale val­ue ten years in the future. Debt amor­ti­za­tion may build equi­ty, but it may reduce cur­rent dis­tri­b­u­tions. Lever­age may increase return on equi­ty, but it also increas­es down­side risk. Cap-rate com­pres­sion may improve returns, but it should not be assumed. The RIA should help the client iden­ti­fy how much of the pro­ject­ed return depends on con­trol­lable oper­at­ing per­for­mance ver­sus mar­ket con­di­tions. A port­fo­lio built on aggres­sive appre­ci­a­tion assump­tions may appear attrac­tive but offer lim­it­ed down­side pro­tec­tion.

Risk Tolerance Versus Risk Capacity

Risk tol­er­ance describes how much volatil­i­ty or uncer­tain­ty the client is emo­tion­al­ly will­ing to accept. Risk capac­i­ty describes how much loss the client can finan­cial­ly with­stand.

These are not the same.

A wealthy investor may have a high capac­i­ty for risk but a low tol­er­ance for uncer­tain­ty. Anoth­er investor may be com­fort­able with aggres­sive invest­ments but depend heav­i­ly on port­fo­lio income and there­fore have lim­it­ed capac­i­ty for loss. Real estate investors may also under­es­ti­mate risk because prop­er­ty val­ues are not quot­ed dai­ly. A prop­er­ty may appear less volatile than a stock port­fo­lio sim­ply because it is appraised infre­quent­ly. That does not mean the eco­nom­ic risk is low­er. The RIA should account for:

This broad­er per­spec­tive helps pre­vent the client from treat­ing illiq­uid­i­ty as sta­bil­i­ty.

Asset Allocation

Asset allo­ca­tion deter­mines how the port­fo­lio is divid­ed among broad cat­e­gories of invest­ments.

These may include:

For a real estate investor com­plet­ing a Sec­tion §1031 exchange, asset allo­ca­tion may be con­strained by the desire to defer gain. That con­straint does not elim­i­nate the need for allo­ca­tion analy­sis. It makes the analy­sis more impor­tant. The client may be con­sid­er­ing plac­ing all exchange pro­ceeds into anoth­er large prop­er­ty. Before doing so, the RIA should eval­u­ate:

A ful­ly deferred exchange may be tax-effi­cient but leave the investor with exces­sive con­cen­tra­tion. A par­tial exchange, direct-prop­er­ty-and-DST com­bi­na­tion, or oth­er coor­di­nat­ed strat­e­gy may bet­ter bal­ance the port­fo­lio.

Strategic Versus Tactical Allocation

Strate­gic asset allo­ca­tion reflects the client’s long-term tar­get. Tac­ti­cal allo­ca­tion involves short­er-term adjust­ments based on mar­ket con­di­tions or spe­cif­ic oppor­tu­ni­ties. A §1031 exchange should gen­er­al­ly be eval­u­at­ed with­in the strate­gic allo­ca­tion. The client should not allow a 45-day iden­ti­fi­ca­tion dead­line to rede­fine the entire long-term port­fo­lio. For exam­ple, sup­pose the client’s strate­gic plan calls for:

If the client already holds 65% of net worth in real estate, rein­vest­ing all sale pro­ceeds into anoth­er prop­er­ty may increase the imbal­ance. The tax ben­e­fit may be valu­able, but the allo­ca­tion risk should be rec­og­nized. The RIA can mod­el the port­fo­lio before and after the pro­posed exchange. This allows the client to see whether the trans­ac­tion moves the port­fo­lio clos­er to or far­ther from the intend­ed strat­e­gy.

Alternative Investments

Alter­na­tive invest­ments include assets out­side tra­di­tion­al pub­licly trad­ed stocks, bonds, and cash.

They may include:

The RIA should not treat “alter­na­tive” as syn­ony­mous with “diver­si­fy­ing.” An invest­ment is diver­si­fy­ing only if its under­ly­ing eco­nom­ic expo­sures dif­fer mean­ing­ful­ly from the client’s exist­ing hold­ings. A pri­vate real estate fund invest­ing in apart­ments may not sig­nif­i­cant­ly diver­si­fy a client who already owns mul­ti­ple apart­ment prop­er­ties. The struc­ture is dif­fer­ent. The risk may not be.

Evaluating Delaware Statutory Trusts as Alternatives

DSTs occu­py a unique posi­tion (Rev. Rul. 2004–86, 2004–2 C.B. 191; SEC, 2022) because they may serve both as:

The RIA should avoid eval­u­at­ing the DST sole­ly on whether it solves an exchange require­ment. The cen­tral ques­tion remains:

“Does this DST improve the client’s total port­fo­lio?”

A DST may reduce direct man­age­ment bur­den while adding expo­sure to a new region or asset class. It may also increase over­all real estate con­cen­tra­tion. Both real­i­ties can exist at the same time.

Institutional Diversification

Insti­tu­tion­al investors often diver­si­fy across:

Indi­vid­ual investors fre­quent­ly lack the cap­i­tal or access need­ed to repro­duce that struc­ture through direct own­er­ship. Frac­tion­al invest­ments, DSTs, and pri­vate funds may pro­vide access to a broad­er range of assets. For exam­ple, an investor sell­ing one local apart­ment prop­er­ty might allo­cate replace­ment cap­i­tal among:

It may reduce depen­dence on a sin­gle asset, mar­ket, ten­ant, or spon­sor. Insti­tu­tion­al diver­si­fi­ca­tion is not mere­ly about own­ing more prop­er­ties. It involves diver­si­fy­ing the under­ly­ing risk fac­tors.

Diversification by Sponsor and Manager

Investors often focus on prop­er­ty diver­si­fi­ca­tion while over­look­ing spon­sor con­cen­tra­tion. A client may own sev­er­al DSTs in dif­fer­ent states and asset class­es but have all of them man­aged by one spon­sor. This cre­ates expo­sure to:

Man­ag­er diver­si­fi­ca­tion can be as impor­tant as prop­er­ty diver­si­fi­ca­tion.

Correlation

Cor­re­la­tion mea­sures how invest­ments move in rela­tion to one anoth­er (Markowitz, 1952). Assets with high pos­i­tive cor­re­la­tion tend to per­form sim­i­lar­ly. Assets with low­er or neg­a­tive cor­re­la­tion may respond dif­fer­ent­ly to eco­nom­ic con­di­tions. The pur­pose of diver­si­fi­ca­tion is not sim­ply to increase the num­ber of hold­ings. It is to com­bine assets whose risk and return dri­vers are not iden­ti­cal. Real estate may have low­er cor­re­la­tion with pub­lic equi­ties over cer­tain peri­ods, but that rela­tion­ship is not con­stant. Real estate and stocks may both be affect­ed by:

Office and mul­ti­fam­i­ly may both be affect­ed by region­al employ­ment. Hos­pi­tal­i­ty and retail may both be affect­ed by trav­el and dis­cre­tionary spend­ing. Senior hous­ing and med­ical office may both be affect­ed by health­care trends. The RIA should exam­ine the actu­al eco­nom­ic dri­vers rather than rely­ing on asset-class labels.

Hid­den Cor­re­la­tion

Clients may believe they are diver­si­fied because they own sev­er­al dif­fer­ent invest­ments. How­ev­er, those invest­ments may share hid­den expo­sures. Con­sid­er a client who owns:

Although the assets appear dif­fer­ent, they may all depend on the same region­al econ­o­my. A local down­turn could affect:

The same analy­sis should apply when select­ing replace­ment prop­er­ty. Adding anoth­er prop­er­ty in the same mar­ket may deep­en the client’s exist­ing eco­nom­ic expo­sure even if the prop­er­ty type dif­fers.

Correlation and Income Sources

Diver­si­fi­ca­tion should also con­sid­er where the client’s income orig­i­nates. A retired investor may receive income from:

If most of these sources are sen­si­tive to the same eco­nom­ic con­di­tions, the income plan may be less sta­ble than it appears. For exam­ple, sev­er­al real estate hold­ings may all face declin­ing occu­pan­cy dur­ing a reces­sion. A port­fo­lio of div­i­dend stocks may also reduce dis­tri­b­u­tions. A well-con­struct­ed income plan should com­bine sources with dif­fer­ent char­ac­ter­is­tics and tim­ing.

Liquidity Planning

Liq­uid­i­ty is the abil­i­ty to access cap­i­tal when need­ed with­out accept­ing an exces­sive dis­count or dis­rupt­ing the broad­er finan­cial plan. Real estate is gen­er­al­ly illiq­uid. DST inter­ests and pri­vate funds are also typ­i­cal­ly illiq­uid and may lack active sec­ondary mar­kets (SEC, 2022). A client com­plet­ing a ful­ly deferred exchange may invest near­ly all avail­able equi­ty into assets that can­not be read­i­ly sold. This can cre­ate prob­lems when the client lat­er needs mon­ey for:

The RIA should deter­mine how much liq­uid­i­ty the client requires before allo­cat­ing cap­i­tal to replace­ment prop­er­ty.

Liquidity Is Not Idle Capital

Clients some­times view cash as unpro­duc­tive. They may want every dol­lar invest­ed. How­ev­er, liq­uid­i­ty has eco­nom­ic val­ue.

It pro­vides:

A client with ade­quate liq­uid­i­ty may be able to hold illiq­uid invest­ments through dif­fi­cult peri­ods. A client with­out liq­uid­i­ty may be forced to sell at the worst time. The RIA should treat liq­uid­i­ty as a strate­gic allo­ca­tion, not as an invest­ment fail­ure.

Liquidity Tiers

A use­ful plan­ning frame­work divides liq­uid­i­ty into tiers.

Immediate Liquidity

Funds avail­able for cur­rent expens­es, emer­gen­cies, and near-term oblig­a­tions.

Exam­ples may include:

Intermediate Liquidity

Assets that can gen­er­al­ly be accessed with­in months or sev­er­al years with­out dis­rupt­ing long-term plans.

Exam­ples may include:

Long-Term Illiquid Capital

Assets expect­ed to remain invest­ed for many years.

Exam­ples may include:

The client should have suf­fi­cient resources in the first two tiers before mak­ing sub­stan­tial com­mit­ments to the third.

Tax Liquidity

Tax defer­ral does not elim­i­nate the need for tax liq­uid­i­ty. A client may need funds for:

The RIA should coor­di­nate with the CPA to ensure that invest­ment allo­ca­tions do not leave the client unable to meet fore­see­able tax lia­bil­i­ties. A strat­e­gy that max­i­mizes invest­ed cap­i­tal but cre­ates a future liq­uid­i­ty cri­sis is not opti­mized.

Income Planning

Income plan­ning deter­mines how the client’s spend­ing needs will be fund­ed over time. For real estate investors, cur­rent rental income may have sup­port­ed the client for many years. After a sale, the replace­ment strat­e­gy must be eval­u­at­ed for its abil­i­ty to con­tin­ue that income.

The RIA should assess:

Alter­na­tive­ly, the client may have suf­fi­cient out­side income and pri­or­i­tize growth. The port­fo­lio should reflect the actu­al need.

Current Income Versus Total Return

Cur­rent income and total return are relat­ed but dif­fer­ent. An invest­ment may pro­duce:

Like­wise, a client seek­ing long-term growth should not nec­es­sar­i­ly select the high­est cur­rent dis­tri­b­u­tion. The RIA should eval­u­ate the sus­tain­abil­i­ty and source of the income. High dis­tri­b­u­tions may be sup­port­ed by:

The client should under­stand whether the dis­tri­b­u­tion rep­re­sents recur­ring eco­nom­ic income or a tem­po­rary pay­ment struc­ture.

Building an Income Floor

For clients depen­dent on port­fo­lio income, the RIA may seek to estab­lish an income floor. This is the lev­el of depend­able income required to cov­er essen­tial expens­es. The income floor may be sup­port­ed by:

More vari­able invest­ments may then sup­port dis­cre­tionary spend­ing and long-term growth. This reduces the pres­sure on any one prop­er­ty or DST to meet all spend­ing needs.

Sequence Risk and Real Estate Income

Sequence-of-returns risk is often dis­cussed in rela­tion to retire­ment port­fo­lios. It can also affect real estate investors.

If a client expe­ri­ences:

dur­ing the first years of retire­ment, the client may need to draw from oth­er assets. Ade­quate liq­uid­i­ty and diver­si­fied income sources can reduce this risk. An investor with all cap­i­tal com­mit­ted to illiq­uid real estate may have few­er options. The RIA should stress-test the income plan for peri­ods of reduced prop­er­ty dis­tri­b­u­tions.

Debt and Portfolio Risk

Lever­age is a major source of both return and risk. A prop­er­ty may appear sta­ble while car­ry­ing sub­stan­tial refi­nanc­ing expo­sure. The RIA should con­sid­er debt at both the prop­er­ty and house­hold lev­el. Rel­e­vant fac­tors include:

Debt across mul­ti­ple invest­ments may also mature at sim­i­lar times. This cre­ates port­fo­lio-lev­el con­cen­tra­tion. A client may own sev­er­al dif­fer­ent prop­er­ties but face simul­ta­ne­ous refi­nanc­ing risk. The RIA should include debt matu­ri­ty sched­ules in the allo­ca­tion analy­sis.

The Role of the RIA in a §1031 Exchange

The RIA should not replace the Qual­i­fied Inter­me­di­ary, CPA, attor­ney, com­mer­cial bro­ker, or secu­ri­ties pro­fes­sion­al. The RIA’s role is to con­nect the trans­ac­tion to the over­all wealth plan.

That role may include:

The RIA may also help the client resist the temp­ta­tion to view the exchange as an iso­lat­ed event.

Questions the RIA Should Ask

A port­fo­lio-focused RIA may ask:

How much of the client’s income depends on one property?

What liq­uid­i­ty will remain after the exchange?

How much debt exposure is appropriate?

What hap­pens if dis­tri­b­u­tions decline? Is the client con­cen­trat­ed in one mar­ket or asset class? Does the client want active con­trol or pas­sive own­er­ship?

How long can the capital remain illiquid?

What are the client’s estate and fam­i­ly objec­tives? Would the pro­posed invest­ment improve or weak­en the over­all port­fo­lio? What invest­ment alter­na­tives are being for­gone? Would the client make the same invest­ment with­out the tax dead­line? These ques­tions expand the dis­cus­sion from tax com­pli­ance to port­fo­lio strat­e­gy. Com­par­ing Replace­ment Strate­gies The RIA can help com­pare mul­ti­ple approach­es.

One Direct Replacement Property

Poten­tial advan­tages:

Multiple Direct Properties

Poten­tial advan­tages:

Poten­tial risks:

Direct Property Plus DSTs

Poten­tial advan­tages:

Partial Exchange

Poten­tial advan­tages:

The RIA should eval­u­ate how each struc­ture affects the total port­fo­lio.

Monitoring After the Exchange

The advi­so­ry role does not end at clos­ing. The RIA should con­tin­ue mon­i­tor­ing:

The replace­ment invest­ment may per­form dif­fer­ent­ly from ini­tial expec­ta­tions.

Income needs may change.

Fam­i­ly cir­cum­stances may evolve.

The port­fo­lio should be reviewed reg­u­lar­ly.

The RIA and After-Tax Wealth Optimization™

With­in the After-Tax Wealth Opti­miza­tion frame­work, the RIA focus­es on the inter­ac­tion among:

The RIA’s respon­si­bil­i­ty is to help ensure that the pre­served cap­i­tal is allo­cat­ed intel­li­gent­ly. A tech­ni­cal­ly suc­cess­ful exchange that leaves the client over­con­cen­trat­ed, illiq­uid, and depen­dent on one source of income may not rep­re­sent an opti­mized wealth strat­e­gy. A coor­di­nat­ed exchange that bal­ances real estate expo­sure with liq­uid­i­ty, diver­si­fi­ca­tion, income, and estate needs may pro­duce a stronger out­come.

Core Principle: Build the Portfolio, Not Just the Replacement Property

The Sec­tion §1031 exchange should not be viewed as a race to replace one prop­er­ty with anoth­er. It should be viewed as an oppor­tu­ni­ty to redesign the client’s cap­i­tal struc­ture. The RIA helps the client move beyond the ques­tion:

“What prop­er­ty should I buy?”

and toward the broad­er ques­tions:

How much real estate should the client own?

What risks should be reduced?

What income is required?

How much liquidity should remain?

Which invest­ments pro­vide gen­uine diver­si­fi­ca­tion? How should the assets ulti­mate­ly trans­fer to heirs? This is the dif­fer­ence between select­ing a replace­ment prop­er­ty and con­struct­ing a wealth strat­e­gy. A strong port­fo­lio does not depend upon one prop­er­ty, one mar­ket, one ten­ant, one spon­sor, or one eco­nom­ic out­come. It com­bines assets inten­tion­al­ly so that income, growth, liq­uid­i­ty, risk, and lega­cy objec­tives work togeth­er. The RIA’s val­ue is not lim­it­ed to man­ag­ing a secu­ri­ties account. The RIA can help ensure that every major cap­i­tal decision—including a Sec­tion §1031 exchange—supports the client’s com­plete finan­cial life.

That is the essence of After-Tax Wealth Opti­miza­tion.

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