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Are Your Investment Goals Unrealistic? Goldstone Financial Group Weighs In

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How much should American retirees temper their investment expectations against market fluctuations? 

If you had posed the question this time last year, you probably would have received a flurry of cautiously optimistic responses as investors looked forward to what they had every reason to believe would be another bull market year. Optimism was rampant — and exciting for investors and retirees, who saw the climbing Dow as a sign that they would be able to live out their sunset years with comfortably-padded retirement accounts

“Nobody in the financial sector wanted to bring people down with dire predictions when the market appeared to be doing so well,” Anthony Pellegrino, the owner and co-founder at Goldstone Financial Group, noted of the mentality at the time. “Investors get fired up when they see reports of record highs.”

“I remember in 2015, there was major pushback from financial professionals when experts at Research Affiliates analyzed financial data from the preceding century and reported that it would be ‘optimistic’ to plan for even a five percent long-term return on a traditional portfolio. People were shocked — and a lot of them rejected those projections as being overly cautionary when the market remained strong.”  

And at the close of 2019, the market’s strength appeared to be on-track to persist. But within the first few weeks of the new year, the Covid-19 pandemic upended the global economy and caused the Dow to plummet. Ten months have since passed, and both have begun to recover.

“It’s not so much about good vs. bad news,” Ryan Detrick, senior market strategist at LPL Financial, recently told USA Today. “The economy is still nowhere near its output prior to the pandemic. But things are getting better.”

However, amid that improvement, those saving for retirement have been forced to question whether the need to revise their expectations for their accounts. The pandemic has demonstrated the dangers of assuming that good times will continue indefinitely — but how pessimistic should investors be about the future?

“This conversation always reminds me of the letter that Warren Buffett sent to his shareholders in early 2008,” Goldstone Financial Group’s Anthony Pellegrino says of expectation-setting. “Back then, he told people to check their perceptions of Dow growth and warned about the dangers of taking those increases out of context. That advice remains just as relevant — if not more so — today.” 

For context, here’s the passage that Pellegrino references from Buffet’s 2008 letter:

“During the 20th Century, the Dow advanced from 66 to 11,497. This gain, though it appears huge, shrinks to 5.3% when compounded annually […] For investors to merely match that 5.3% market-value gain, the Dow — recently below 13,000 — would need to close at about 2,000,000 on December 31, 2099 […] I should mention that people who expect to earn 10% annually from equities during this century — envisioning that 2% of that will come from dividends and 8% from price appreciation — are implicitly forecasting a level of about 24,000,000 on the Dow by 2100.”

“If your adviser talks to you about double-digit returns from equities,” Buffett concluded, “Explain this math to him.”

When taken into consideration alongside the uncertainty posed by Covid-19, Buffett’s math provides investors with ample reason to be careful. But what measures can aspiring retirees take to protect themselves and their accounts? 

Goldstone Financial Group’s Anthony Pellegrino points to three main strategies — consulting a fiduciary advisor, exploring IRA opportunities, and moving away from a buy-and-hold norm. 

Consulting a Fiduciary

Are you intimidated by market fluctuations and want a professional’s help in navigating them? A fiduciary advisor can help. 

“I cannot stress the importance of finding a fiduciary advisor enough,” Pellegrino emphasizes. “If you opt for a non-fiduciary professional, well, I’ll borrow another Buffett quote — ‘beware the glib helper who fills your head with fantasies while he fills his pockets with fees.’”

A fiduciary advisor is a financial professional who is legally obligated to act in their client’s best interests. They can only purchase and sell investments that they believe are well-suited to their clients’ needs and goals, and they cannot base their decisions on whether their suggested investments would provide the best kickbacks. 

As writers for NerdWallet summarize: “Fiduciaries are held to a significant level of trust with their clients and must avoid conflicts of interest. If your financial advisor does not have a fiduciary duty to you, they may be able to recommend investments or products that pay them a bigger commission over ones that would be the best fit for you, which could cost you more.”

Every single investment advisor employed at Goldstone Financial Group is a certified fiduciary advisor. The logic behind this policy is simple. 

“We want our clients to get the best possible advice,” Anthony Pellegrino says. “Having advisors who are held to a fiduciary standard ensures that they receive exactly that.” 

Explore IRA Opportunities

Think you can’t touch the money in your 401(k) until you retire? Think again! Pellegrino and the fiduciary advisors at Goldstone Financial Group often suggest that their clients withdraw a portion of their account balance and roll it over into an IRA account. The benefits of this tactic, Pellegrino says, include increased flexibility with investments.

“A nontaxable rollover to an IRA would give you more freedom to work with your financial advisor in choosing investments,” Pellegrino explains. “That said, you should always consult with your tax professional about potential tax implications before embarking on this strategy.”

Rethink Buy-and-Hold

Making investments and holding onto them indefinitely isn’t always the best strategy for long-term growth. 

“You may want to opt for tactical managed asset accounts that will allow you to capture and participate in the stock market’s upside and then, when the market declines, shift your assets to cash,” Goldstone Financial Group’s Anthony Pellegrino suggests. “Sure, you may still experience a loss — but typically, you’ll lose less than you would with a buy-and hold-strategy.” 

At the end of the day, Pellegrino offers one piece of advice that supersedes all others. 

“Don’t go through this alone. Your situation is unique, and the solutions you need will be equally so. Consult with a fiduciary advisor to see how your expectations and plans stack up against market conditions.” 

The idea of Bigtime Daily landed this engineer cum journalist from a multi-national company to the digital avenue. Matthew brought life to this idea and rendered all that was necessary to create an interactive and attractive platform for the readers. Apart from managing the platform, he also contributes his expertise in business niche.

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Business

Royal York Property Management And Nathan Levinson On Building Stable Rental Portfolios In A Volatile Market

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Across North America, Europe, and much of the world, rental housing is caught between two pressures. On one side are tenants facing record affordability challenges. On the other side are landlords seeing operating costs, interest payments, and regulatory complexity move in the opposite direction.

Recent analysis from Canada’s national housing agency shows how tight conditions still are. The average vacancy rate for purpose-built rentals in major Canadian centres rose to about 2.2 percent in 2024, up from 1.5 percent a year earlier, but still below the 10-year average despite the strongest growth in rental supply in more than three decades. 

At the same time, higher interest rates have pushed up the cost of acquiring and financing rental buildings, which has slowed transactions and made many projects harder to pencil out.

In this environment, the question for landlords and investors is less about chasing maximum rent and more about building stability. That is where Royal York Property Management and its founder, president, and CEO Nathan Levinson have drawn attention.

From a base in Toronto, Royal York Property Management manages more than 25,000 rental properties, representing over 10 billion dollars in real estate value, and operates across Canada, the United States, and parts of Europe. Levinson also sits on a Bank of Canada policy panel focused on the rental market, where he provides data and on-the-ground insights about rent trends and landlord stress. 

For many smaller property owners, his model has become a reference point for how to treat rental housing as a structured financial asset rather than a side project.

Rental housing under pressure from both sides of the balance sheet

In many countries, the basic rental story is the same. Construction of new rental housing has climbed, yet demand still runs ahead of supply in most major cities. In Canada, overall rental supply grew by more than 4 percent in 2024, the strongest increase in over thirty years, while vacancy rose only modestly. 

At the same time, borrowing costs have moved sharply higher compared with the pre-pandemic period. Research shows that elevated interest rates have reduced the profitability of new multifamily deals and slowed investment activity, even as structural demand for rental housing stays strong.

For small and mid-sized landlords, that tension shows up in a simple way. Mortgage payments, taxes, insurance, and maintenance rarely move down. Rents move up more slowly, and in many jurisdictions they are constrained by regulation or market realities.

Levinson’s view is that this gap will not close on its own. Landlords who want to stay in the market need more predictable income, tighter control of costs, and clearer systems for dealing with risk.

A property management model built for volatility

Royal York Property Management did not start as an institutional platform. Levinson’s early clients were owners of single condominiums, duplexes, or small buildings who were struggling with irregular rent payments, surprise repairs, and complex rental rules.

Instead of handling each property ad hoc, he built a standardized operating model that treats every door as part of a wider portfolio. Each unit sits on a centralized platform that records rent, arrears, lease expiries, maintenance tickets, and legal actions. Owners see real-time statements and performance metrics rather than waiting for year-end reports.

That structure, combined with an internal maintenance and legal team, is designed to handle stress rather than avoid it. When markets are calm, the system may look conservative. When conditions worsen, it is what keeps owners in the black.

“Execution is everything” is how Levinson often frames it in interviews. 

Turning rent into a more predictable income stream

The feature that first drew many investors to Royal York Property Management is its rental guarantee program in Ontario. Under this model, landlords receive their rent even if a tenant stops paying. RYPM takes responsibility for legal proceedings, arrears recovery, and re-leasing the unit, while the owner continues to receive income.

Independent profiles of the company describe this as one of the first large-scale rental guarantee frameworks in the Canadian market, and note that the firm manages tens of thousands of units under this structure. 

The guarantee itself is closely tied to local law and does not transfer directly into every jurisdiction. The underlying logic, however, is straightforward:

  • Treat unpaid rent as a recurring and manageable risk rather than an occasional shock.
  • Price that risk into a clear product instead of handling each case informally.
  • Use scale, legal expertise, and data to keep default rates low and resolution times shorter.

For landlords who are facing mortgage renewals at higher interest rates, having a more stable rent stream can be the difference between holding a property and being forced to sell. That is one reason rental guarantee models have started to attract interest from investors outside Canada who are watching RYPM’s approach.

Using technology to see risk earlier

Behind the guarantee and the day-to-day operations is a technology stack that tries to surface problems before they become crises. Royal York Property Management’s internal platform uses data from payments, maintenance, and tenant behavior to flag risk signals and operational bottlenecks. 

Examples include:

  • Tenants who move from on-time payments to repeated short delays.
  • Units where small repair tickets point to a larger capital issue ahead.
  • Buildings where complaint volumes suggest service gaps or staffing problems.

Rather than treating these as isolated events, the system aggregates patterns across thousands of units. That allows management to decide whether a problem is individual, building-specific, or systemic.

Levinson has also pushed this data outward. As a member of the Bank of Canada’s rental policy panel, he provides anonymized information on rent collection, defaults, and renewal behavior, which feeds into broader discussions about financial stability and housing policy. 

The same data that protects a landlord’s cash flow in one building helps central bankers understand how higher rates are affecting thousands of households.

Why the Canadian case matters for global landlords

Several recent reports underline how closely rental markets are now tied to national economic performance. Tight rental supply and high rents are feeding inflation in many economies. At the same time, higher borrowing costs are discouraging new construction, which risks prolonging shortages. 

This feedback loop is especially hard on small landlords. Many own only one or two properties and have limited room to absorb higher mortgage payments or extended vacancies. Analysts in Canada and abroad have warned that some owners are at risk of default as their loans reset at higher rates. 

In that context, the Royal York Property Management model offers three lessons that travel across borders:

  1. Standardization protects both sides. Clear processes for screening, rent collection, maintenance, and legal steps reduce surprises for owners and tenants at the same time.
  2. Risk pooling is more efficient than one-off crises. Handling arrears, legal disputes, and vacancies inside a structured system is less costly than improvising each time.
  3. Operational data belongs in policy conversations. When policymakers have access to real rental data rather than only mortgage statistics, interventions can be better targeted.

It is not an accident that Levinson’s work now sits at the intersection of private property management and public financial policy.

What everyday landlords can borrow from the Royal York playbook

Most landlords will not build a 25,000-unit management platform. Many will never interact with a central bank. The core ideas behind Nathan Levinson’s approach are still accessible to smaller owners that manage a handful of properties.

Three practices stand out.

First, treat every rental unit as part of a simple portfolio. That means using a consistent template to track rent, arrears, expenses, and vacancy days for each property, then reviewing it on a schedule instead of only when something goes wrong.

Second, write down the rules for risk in advance. Late-payment steps, repayment plans, documentation standards, and maintenance response times should exist on paper, not only in memory. Royal York’s experience suggests that clear rules reduce conflict, because everyone knows what will happen next. 

Third, invest in service as a protective layer. Multiple independent profiles of RYPM point out that faster response times and transparent communication reduce tenant turnover and protect building condition, which in turn supports long-term returns. 

For landlords and investors trying to navigate today’s volatile rental markets, the message from Royal York Property Management and Nathan Levinson is surprisingly simple. You cannot control interest rates or national housing policy. You can control how organized your portfolio is, how clearly you manage risk, and how consistent your operations feel to the people who live in your buildings.

For many, that shift from improvisation to structure is what will decide whether their rental properties remain a source of wealth or turn into a source of stress.

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