Cain Brothers Newsletters: Industry Insights

<p>Cain Brothers Newsletters: Industry Insights</p>

“Industry Insights” is a bi-weekly email newsletter published by Cain Brothers, a division of KeyBanc Capital Markets. The newsletter features innovative and original perspectives about healthcare services, healthcare IT, and life sciences from our team of experienced investment bankers. Read the latest newsletter content below, and subscribe to start receiving the newsletter in your inbox.

Asset Monetizations for For-profit Senior Living Owner-Operators

Kyle Hemminger

April 29, 2026 – Banker Commentary by Kyle Hemminger

As for-profit owner-operators of senior living communities, including both seniors housing and skilled nursing, evaluate their strategic alternatives, they may consider the asset monetization financing structure which, in the simplest terms, is akin to a sale-“manageback” transaction as opposed to a sale-leaseback (triple-net lease) structure. This financing structure has many similarities to an outright sale, with some important attributes and considerations.

In an asset monetization, the real estate and operations are sold to a not-for-profit organization. Owner-operators can either partner with an existing not-for-profit or form a new not-for-profit organization, subject to certain restrictions. To facilitate the purchase of the real estate and operations, the not-for-profit acquirer accesses capital via the tax-exempt bond market, often utilizing a senior-subordinate capital structure in which the senior bonds are sold to institutional bond funds and the for-profit seller receives the subordinate, tax-exempt bonds. As consideration for the sale, the for-profit seller receives cash from proceeds of the sale of the senior bonds and the subordinate, tax-exempt bonds (seller financing). While both the real estate and operations are sold to the nonprofit acquirer, the for-profit seller typically also enters into a long-term management agreement to provide day-to-day operational oversight to the nonprofit acquirer post-closing. Since the acquisition financing is largely driven by debt service coverage, this structure lends itself to stabilized assets with EBITDAR margins exceeding 30%.

The asset monetization structure has many key attributes, including a longer term for the management agreement (often multiple years and subject fair market terms). In this regard, the for-profit seller is able to preserve their home office staff, continue to run the day-to-day operations of the communities, and preserve the legacy of the company, which is a key consideration for many privately held family businesses. Further, via the subordinate tax-exempt bond seller financing, the for-profit seller receives tax-advantaged interest payments until maturity of the bonds. As such, the for-profit seller has some latitude to manage potential capital gains by taking more subordinated bonds at closing.

Like many strategic alternatives, however, there are important trade-offs. For example, the asset monetization structure does not work for negative cash flow communities and is generally discouraged for low EBITDAR margin businesses, since any growth in cash flow and/or appreciation in the value of the assets will only benefit the nonprofit if the assets are sold prior to stabilization. Additionally, there are meaningful transaction costs incurred in structuring and executing an asset monetization, so scale (EBITDAR exceeding $8-10 million) is important. This structure can also be problematic for sellers with institutional capital, as institutional investors generally prefer the entire purchase price to be paid in cash at closing, rather than a mixture of cash and seller financing. Finally, like with all debt financing, this structure is subject to market conditions, so interest rates and investor demand must be considered.

An asset monetization presents an elegant, customizable solution for for-profit organizations considering a sale of their real estate and operations. The structure can be utilized for select assets or an entire portfolio. As is often the case with strategic decisions, however, an asset monetization has important attributes and considerations.

Recent Deals

March 2026

bcdsk

affiliated with

highmark

Financial Advisor

blue-cross-blue-shield-kansas-city
March 2026

dme express

acquired by

palladium equity partners

Sell-Side Advisor

dme-express-acquired-by-palladium-equity-partners
March 2026

supercare health

acquired by

excellere

Sell-Side Advisor

supercare-health-excellere-partners
March 2026

supercare health

Joint Lead Arranger
Joint Bookrunner
Administrative Agent

supercare-health-excellere
February 2026

hlsg

acquired by

sterling group

Sell-Side Advisor

hlsg-acquired-by-sg
February 2026

cmh

affiliated with

prime hc foundation

Sell-Side Advisor

cmh-and-phf
February 2026

thermo fisher scientific

$1 Billion

Senior Notes due 2031

$750 Million

Senior Notes due 2033

$1.3 Billion

Senior Notes due 2036

$750 Million

Senior Notes due 2046

Co-Manager

thermo-fisher-scientific
February 2026

my town health partners

acquired

mdb

Buy-Side Advisor

mytown-health-partners
January 2026

nrad

acquired by

premier

Sell-Side Advisor

national-radiology-solutions-premier-radiology
January 2026

tenor

acquired

commonwealth health

Buy-Side Advisor

tenor-health-to-acquire-commonwealth-health
December 2025

fhn

affiliated with

mercy health

Sell-Side Advisor

fhn-memorial-hospital-mercyhealth
December 2025

US Fertility

acquired

genetics IVF

and was recapitalized by

I Catterton

and

amulet

$1.07 Billion

Senior Secured Credit Facilities

Joint Lead Arranger
Joint Bookrunner
Administrative Agent

us-fertility-completes-debt-refinancing

Cain Brothers, a division of KeyBanc Capital Markets is a trade name of KeyBanc Capital Markets Inc., Member FINRA/SIPC.

KeyBanc Capital Markets Inc. and KeyBank National Association (“KeyBank N.A.”) are separate, but affiliated companies. Securities products and services are offered by KeyBanc Capital Markets Inc. and its licensed securities representatives. Banking products and services are offered by KeyBank N.A.

Securities products and services: Not FDIC Insured • No Bank Guarantee • May Lose Value

Please read our complete KeyBanc Capital Markets disclosure statement.

Connect With Us

Find an Expert