The affordable housing crisis continues to be one of the most pressing challenges in cities across North America. While policymakers debate large-scale solutions, innovative real estate investors are experimenting with new models that maximize both profitability and social impact. Among them is Dr. Connor Robertson, a Canadian-born entrepreneur and real estate investor who has built a reputation for identifying untapped opportunities in commercial and multifamily housing.
Dr. Robertson argues that reimagining how existing properties are used can unlock significant value for communities and investors alike. “What we’re working on right now is combining our experience in the short-term rental space with mid-term rentals and pad splits,” he explains. “By converting motels or multifamily units into more flexible housing, we’re able to create affordable living options while still maintaining strong returns.”
From Health to Housing
Dr. Robertson’s professional journey is far from conventional. Trained as a chiropractor with a doctorate from New York Chiropractic College, he initially built a career focused on health and wellness before transitioning into real estate. His background in healthcare, he says, has sharpened his ability to understand systemic challenges and apply data-driven strategies, skills that he now uses to navigate complex property deals. As a co-founder of a real estate firm, Dr. Robertson has been instrumental in transforming short-term rental markets by leveraging technology and strategic insights. Today, his focus has shifted toward tackling the affordable housing shortage by converting underperforming motels into shared housing units that align with community needs.
The Financial Logic Behind PadSplit
At the heart of Dr. Robertson’s strategy is one economic principle: net operating income (NOI) drives property valuation in commercial real estate. Traditional long-term rentals may generate steady income, but they often fall short of maximizing a property’s potential. A case in point is a 30-unit property Dr. Robertson is working on in New Orleans. “If we were to rent that property long-term, we’d get around $28,000 a month in income,” he says. “As a motel, it’s actually losing money. But if we convert it into pad splits at $185 to $250 per week, the income rises significantly. That allows us to stabilize the property, refinance, and ultimately increase its value.”
By diversifying tenants into smaller, affordable units, pad splits spread risk across multiple occupants. If one tenant leaves, the space can be quickly filled by another, reducing the vacancy risks that often plague traditional rentals. “You get this diversification of risk because you have a platform like PadSplit that generates demand and replaces tenants quickly.”
Risk, Reward, and Community Impact
These projects require careful planning and execution. Commercial real estate financing is often more complex than residential, with shorter loan terms and more variables to manage. Still, Dr. Robertson believes the potential rewards justify the effort. “It’s not easy. These are bigger transactions with a lot of moving parts—financing, negotiation, structuring, renovations. But when you stabilize the income and refinance, you can get all your money back out and still have a strong cash-flowing asset,” he says. Beyond the numbers, he emphasizes the social benefits. Padsplits provide flexible, affordable housing options for individuals who may not qualify for traditional leases or who need temporary accommodations. In cities grappling with housing shortages, these conversions can add much-needed capacity while offering investors attractive returns.
A Blueprint for the Future
Dr. Robertson’s approach represents a blueprint for rethinking commercial real estate in ways that address urgent social challenges. By blending the mechanics of hospitality with the stability of long-term rentals, his projects demonstrate how creative strategies can generate both financial and community value. “Real estate is about solving problems,” Dr. Robertson says. “If you can create affordable housing while also making a property more profitable, that’s a win for everyone.”
For more insights from Dr. Connor Robertson, connect with him on LinkedIn or visit his website.
