Section 1031 Like-Kind Exchanges Guidance, Strategies and Solutions. What are they? Examples of what we can do and how we can help others.

1. Section 1031 Like-Kind Exchanges
Guidance ● Strategies ● Solutions
Business Banking Presentation July 10, 2013

2. Services
• Forward Exchanges
• Reverse Exchanges
• Improvement Exchanges
• Replacement Property Strategies
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3. Like Kind Exchanges
Types of Assets Commonly Exchanged
• Real Estate (fee, easements, long-term leaseholds)
• Mineral interests (royalties, leaseholds)
• Aircraft
• Vehicles
• Equipment
• Rolling stock
• Intangibles (licenses, brands, franchise or distribution rights)
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4. Representative Transactions
$1.30 Billion Forward Exchange on 5 Times Square, NYC
$1.25 Billion Forward Exchange on 280 Park Avenue, NYC
$1 Billion Reverse Exchange on 399 Park Avenue, NYC
$300 Million Reverse Exchange on Westin Waterfront Hotel, Boston
$300 Million Forward Exchange on Portfolio of Multifamily assets
$234 Million Forward Exchange on Riverfront Plaza, Richmond VA
$230 Million Forward Exchange on Long Wharf Marriot, Boston
$225 Million Forward Exchange on One California Plaza, Los Angeles
$207 Million Forward Exchange on 100 East Pratt Street, Baltimore
$205 Million Forward Exchange on 5 Embarcadero Center, San Francisco
$45 Million Forward exchange of development rights
$150MM Reverse exchange involving Fortune 50’s replacement of its fleet of Gulfstream aircraft
$33 Million Reverse exchange of Oil & Gas rights
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5. • Forward Exchange
• Reverse exchange
• Related Party Exchange Rules
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Like Kind Exchange Basics

6. Forward Exchange – Used When:
• Client is selling a business or investment property.
• Client intends to replace it with new business or investment
property.
• Old property will be sold before the new property is acquired.
• In a forward exchange, we hold FUNDS.
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7. Reverse Exchange – Used When:
• Client is selling a business or investment property.
• Client intends to replace it with new business or investment
property.
• New property will be acquired before the old property is sold.
• In a reverse exchange, we hold PROPERTY.
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8. Improvement Exchange - Used When:
• Client is selling a business or investment property.
• Client intends to replace it with new business or investment
property.
• FMV of new property < FMV of old property
• The new property will be improved, and the increased value is
needed to defer gain.
• In an improvement exchange, we hold property, and build on
it.
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9. 9
Like-Kind Exchange- Property Limitations
• Property must be:
– “Held for” -- means it must have been owned for some time
– Business or investment
– Excludes dealer property, inventory, stock and securities
• Like-Kind Standard
– Real estate-very broad, improved or not, type of improvements or
use does not matter
– Personal property-like class or like-kind (more restrictive)

10. 10
Like-Kind Exchange-Computational Rules
• RP must be of equal or greater value.
• All of the net proceeds from the RQ must be invested in the
RP.
• Must cover all the debt on RQ with debt on the RP or
additional cash (mortgage boot).
• If there’s a shortfall, the exchange is partially taxable.
However, if the value of the RP is less than the taxpayer’s
basis in the RQ, then it’s FULLY taxable.

11. Forward Exchange – “Down Leg”
• Before closing, T enters into exchange agreement with QI.
• T assigns its rights under the P&S to the QI.
• QI sets up a bank account at RTC for T’s exchange.
• QI notifies the buyer of the old property that the sale is part of an
exchange and supplies wiring instructions and instructions for
preparation of the settlement statement.
• T transfers old property directly to buyer (direct deeding).
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12. Common “Down Leg” Issues
• Identity of the taxpayer.
• Qualified use (holding period, mixed use properties).
• Use of funds to pay debts and closing costs. (Prorations, security
deposits, cross-collateralization, defeasance, etc.)
• Seller financing.
• Taxpayer needs some cash at closing.
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13. Forward Exchange-Next Steps
• T has 45 days to identify new property (alternative ID rules: 3
property/200% rules).
• If T does not identify, exchange ends on Day 46
• Once T identifies, the funds must be held until the end of the 180
days, and can only be used to acquire identified property
• T has 180 days to close on the new property, any unused funds are
then disbursed
• The old and new property must be “like-kind”.
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14. Common Exchange Problems
• Taxpayer changes their mind during the ID period and wants the
funds-–must wait until the 45 day ID period expires
• Taxpayer wants to change the ID -–OK during the ID period, but
NOT once the ID period ends
• Taxpayer identifies property, but is unable to close on any of them
and wants the funds early -–funds must sit until after Day 180
• Actual or constructive receipt of any amount from the QI during
the exchange makes the entire transaction taxable, and may cause
the QI to be the taxpayer’s agent, precluding the QI from doing
any further exchanges for the client, and according to the IRS,
other clients as well
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15. Common “Up Leg” Issues
• Sufficient value of replacement property.
• Depreciation recapture on personal property.
• Accuracy of ID.
• Use of funds: deposits, paying loan and due diligence costs.
• Sending the funds to taxpayer’s attorney for closing.
• Amount of financing.
• Title and ownership issues on replacement property.
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16. Reverse Exchanges
• Rev. Proc. 2000-37 establishes a “safe harbor for reverse
exchanges (qualified exchange accommodation arrangements).
• Two principal uses:
– Timing: new property closing prior to old
– Value: Improve the new property while accommodator owns it
• T can receive all of the economic benefits (except tax
depreciation) during the time of the QEAA.
• Accommodator must treat the property as if it is the owner for tax
purposes.
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17. Reverse Exchanges
• Significantly more documents and more risk for the
accommodator.
• Risks mitigated by insuring property and T’s indemnity.
• T, an affiliate or third party lender (or combination) can loan
purchase price.
• T can manage the property or manage the LLC owning the
property.
• Transfer is effected by an option to purchase that is exercised
when the old property sells.
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18. Common Reverse Exchange Issues
• Setting up rents, security deposits.
• Getting rents to the taxpayer for tax purposes.
• Structuring financing on parked replacement property.
• Improvement exchanges- documenting construction expenses.
• Improvement exchanges -disbursement of exchange funds.
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19. Related Party Exchange Rules
• Two related parties can enter into a direct exchange, if each holds
its replacement property for 2 years.
• Taxpayer cannot sell its property to a third party through a QI and
then buy replacement property from a related party (Rev. Rul.
2002-83) using cash held by QI.
• Taxpayer can sell its relinquished property to a related party to
commence an exchange, and the related party does not need to
hold the property for 2 years.
• Taxpayer can buy its replacement property from a third party
PROVIDED that the related party is also doing an exchange.
• THERE ARE MANY STRATEGIC APPLICATIONS OF THESE RULES TO
MINIMIZE TAX LIABILITY!
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20. 20
Rev. Proc. 2008-16
Safe Harbor for Vacation/Rental Homes
• Creates a safe harbor on whether a mixed vacation/rental house is
considered “held for investment.”
• Before this, there was some doubt as to what standard applied. Was
it the “primary” purpose? Did ANY personal use disqualify the property
from §1031?
• The held for investment requirement applies to both RQ and RP.

21. 21
Rev. Proc. 2008-16
RQ Property Requirements:
• Property must have been held for 24 months before the sale.
• During each 12 month period before the sale the property must meet
all of the following:
– The property must have actually been rented out.
– To a person (cannot be related under §267 unless the residence is
the related person’s principal residence).
– For at least 14 days.
– At “fair value.”
• The property cannot have been used for personal purposes for more
than THE GREATER OF:
– 14 days, or
– 10% of the days it was actually rented out.

22. 22
Rev. Proc. 2008-16
RP Property Requirements:
• The same requirements will apply to the RP (24 month hold,
minimum 14 days of fair value rental, and personal use limit).
• The IRS says that if you do not meet the RP requirements, you
should file an amended return claiming that no exchange
occurred. (This should not be the case, it would be outside the
safe harbor, but would not necessarily mean that the exchange
is a failed exchange…)

23. What happens when investment property is
later converted to personal use?
• As long as Rev. Proc. 2008-16 is satisfied, later conversion
to a vacation home is within the safe-harbor and the IRS will
not challenge the exchange on the basis of mixed use
• If taxpayer converts to principal residence, then the Section
125 gain exclusion cannot be claimed until after 5 years
from the acquisition date of that property
• If taxpayer changes use in year 3 and occupies for 2 of the
last 5 years, then the taxpayer may exclude $250K/$500K of
capital gain under Section 125
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24. Case Study #1 –Equipment Dealer
• Customer is selling their old commercial building for
$600,000
• Customer has P&S for land for $100,000 and plans to
construct a new steel building for $500,000
• Compass set-up an “improvement exchange” using the
money from the old building to acquire the new land and
fund the improvements by paying the contractors
• For our fee of $12,500 we saved customer approximately
$150,000 in tax
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25. Case Study #2 – McDonald’s Franchises
• Customer is selling 5 McDonald’s restaurants in Western MA
for $8MM
• Customer had an agreement to buy 7 McDonald’s in CT for
$15MM on the next business day
• Compass set-up an exchange in which we received the
purchase funds from Citizens Bank, and paid off the existing
loan with Chase on the new stores
• For our fee of $7,500 we saved customer $1.0MM in tax
liability
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26. Case Study #3 – Trucking
Company
• Customer is selling several tractors and trailers for $300,000
• Customer is buying a business for $1.0MM that includes
specialized tractors and roll-off trailers
• Using customized exchange documents, we used the funds
to purchase part of the business assets which were “like-
kind” to the tractors and trailers that were sold
• For our fee of $3,500 we saved customer approximately
$130,000 in tax liability
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27. Like Kind Exchanges
Benefits to Rockland Trust
• Fee income
• Balances-can be lumpy but balances nonetheless
• Customer goodwill from a service that is always worth more
than it costs
• Possibility of lending on replacement property side
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28. Like Kind Exchanges
Benefits to the Business Banker
• Opportunity to be a trusted adviser
• Presentations to centers of influence, attorneys and CPAs to build
goodwill
• Help distinguish Rockland Trust from other banks that do not offer
this service, or not at our level of sophistication
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29. Bio
Andrew F. Gelson, Esq. (Managing Director) is responsible for Compass’
strategic, legal, and product development activities. Andy has 27 years of
experience practicing real estate and tax law and specializes in IRC §1031. Prior
to co-founding Compass, he was Senior Vice President and General Tax Counsel at
J.P. Morgan Property Exchange Inc. (JPEX) where he had primary responsibility for
executing more than $20 billion of exchange transactions on behalf of corporate
and institutional property owners.
Andy is admitted to the bar in CA and MA and holds a BS from Boston College, a JD
from Southwestern University, and an LLM (in Taxation) from New York University.
He is also an active member of the American Bar Association (ABA) Tax Section
and the Equipment Leasing and Financing Association and has spoken and written
about various exchange topics, including exchanges of oil and gas properties.
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30. Andrew F. Gelson
Managing Director
Andrew.Gelson@Rocklandtrust.com
Compass Exchange Advisors LLC
2036 Washington Street
Hanover, MA 02339
Tel: 508.830.1188
Direct: 781-982-6738
Fax: 508.830.1288
www.compass1031.com
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