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From Contracts to Counsel: Your Essential Guide to Hiring a Probate Attorney in Chicago

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Like many people, you’ll come across the term probate after a loved one, such as a parent or spouse, passes away. So, what is probate, and why do you need an attorney for it? As defined in Forbes, probate is a legal process that occurs after death. It entails transferring the assets of the decedent (the person who passed) to beneficiaries named in their last will. 

With that in mind, having a probate lawyer by your side is essential. The last thing you want to do is deal with the legal complexities of settling a loved one’s estate while grieving. A probate lawyer oversees the validation of the deceased’s will and the fair distribution of assets among family members. One challenge lies in finding a top-quality probate lawyer.

In this guide to hiring a probate attorney in Chicago, we’ll discuss the tips to identify the right legal professional for probate proceedings. 

Understand the Responsibilities of a Probate Lawyer

It’s difficult to hire a talented probate lawyer when you don’t know what they do: Start by understanding the roles they play. 

When you work with a Chicago probate lawyer, some tasks they might do include: 

  • Act as an estate executor or administrator 
  • Collect proceeds from the life insurance policies of the deceased
  • Identify and secure the decedent’s assets
  • Get an appraisal for the deceased’s estate
  • Pay debts and resolve estate tax issues
  • Prepare and file documents required in probate court
  • Transfer assets to rightful heirs
  • Represent you in litigation proceedings if someone challenges or contests the will

A probate lawyer could also help you and your family navigate state inheritance laws if a loved one dies without a valid will. That way, you can avoid unnecessary taxes or other ramifications of not creating a will, such as losing ownership rights of the deceased’s business or financial support.

Search for Lawyers Online and Offline

You’re probably thinking, where do I find the best lawyer to hire? You could seek referrals from friends or colleagues. Friends who worked with probate attorneys before might provide important details, such as how the lawyers communicate and handle the probate process. 

Alternatively, do a simple online search using the terms “probate lawyer near me” or “probate attorney in Chicago.” Go through various websites or online directories and write names of lawyers with positive ratings and customer testimonials. Then, contact the potential lawyers to set up free consultations. Note that not all legal professionals offer free consultations, so make sure to ask before setting a time in your calendar. 

Ask the Right Questions

A free consultation provides opportunities to ask questions to better understand if the lawyers in question have the qualifications to handle your probate case. 

Four questions you might ask attorneys during the initial meeting may include:

  1. Do You Have Experience in Probate Law? 

When evaluating lawyers, prioritize experience. An experienced probate lawyer is aware of common pitfalls that can result in the probate petition being postponed or dropped by a judge. To feel more comfortable about an attorney’s expertise, ask them if they’ve handled probate cases similar to yours before. 

For example, let’s say the deceased owned a substantial estate or had complicated assets like royalties and mineral stocks. Working with an attorney with a track record of successfully handling cases like that could save you time and money in the long run.

  1. What Do Other Clients Say About You?

Experience alone doesn’t make a probate lawyer perfect for your case. Look for someone with an outstanding reputation. These reviews likely live on Google next to their business profile or are featured on their website. If you can’t find any endorsements, ask for testimonials written by past clients. 

One point to focus on is what reviewers say about the lawyer’s efficiency and speed. Beyond that, does the lawyer offer expert guidance, conflict mitigation, and proper asset management during probate? 

A probate attorney in Chicago, IL, should be an efficient expert in asset preservation. This can be crucial to helping avoid hefty taxes and excessive debt claims. Additionally, if the lawyer receives positive feedback on conflict mitigation, it suggests they have experience in resolving or mitigating family conflicts that tend to stall the probate process. 

  1. How Long Does Probate Last? 

One way to test a probate lawyer’s knowledge is by asking them, “How long does probate last?” While the numbers vary, probate can last for a few months to over a year in many states, including Chicago. When highlighting factors that affect the duration of probate, your counsel might mention things like estate size, family disputes, debt and taxes, absence of a will, and state laws.

A knowledgeable lawyer can explain clearly why your probate case could last a few months or even years. A lawyer that makes too brazen or hard-set of promises might not be the most honest. 

  1. How Do You Want Us To Communicate? 

There’s no hard rule on how you and your probate attorney communicate. You can talk via text messages, email, video calls, or phone calls. More importantly, check that the attorney communicates in simple language to help you understand your case. 

In fact, one essential of a lawyer’s dos and don’ts to gaining clients’ trust is to avoid making clients feel clueless. If a potential lawyer uses complex legal terms or avoids communicating directly, search for probate services elsewhere.

Conclusion: Finding a Probate Attorney in Chicago

Reviewing the will of a loved one after their death and ensuring fair distribution of their assets often involves complex legal issues. For this reason, consider hiring an attorney who specializes in probate law. 

To maximize your chances of finding the right probate lawyer, familiarize yourself with their responsibilities. Next, search online for lawyers within your state or ask for recommendations from people you trust. Then, interview prospects to help ensure they possess experience, a remarkable reputation, communication skills, and knowledge of probate law.

Settling the affairs of a loved one who has passed on can be an overwhelming time. A probate attorney can help lift some of the pressure off your shoulders as you focus on grieving and healing. 

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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