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Bigger Pockets Questions to ask a Property Manager

Bigger Pockets Questions to ask a Property Manager

Not sure about the questions to ask a Property Manager before hiring them. came up with many questions and we answered them for you below.

Are you a licensed property manager?

Yes, we are fully licensed by IL for real estate sales, rentals, and property management.

What certifications do you have? What’s the most recent continuing education course you have completed?

We are part of several trade organizations, the National Association of Real Property Management (NARPM) Chicago Association of Realtors, and the National Association of Realtors, each of them has its own courses that we have to take as well as the state of IL requires all of our brokers to do continuing education every two years. We are also certified in Pest control, and lead-based paint on the maintenance side.

Do you have insurance for your property management business?

Yes, we carry both E&O for the real estate and general liability for the maintenance side.

Have you ever owned rental property?

Due to the recent shift in the market we do not currently own any properties within the company but will be buying once the market is ripe again or the right deal comes along. We also encourage all of our employees to get involved in real estate investing and are looking to start a syndication for us and our clients to be able to buy a bigger property in the near future.

What relevant real estate-related experience did you possess before becoming a property manager?

Our team has worked at several larger property management companies before coming to Chicago Style Management. Our owner has experience in Real estate sales, construction, and insurance in his past careers before doing Property Management.

How long have you been in the property management business?

Chicago Style Management was formed in 2020, however, we were under the Kale Realty umbrella before that and Kale Realty has been around since 2007. Our entire team that was in the PM division at Kale moved over with us.

Which types of properties and neighborhoods do you specialize in?

 We specialize in C and D-class properties, as well as properties that need some love to get back to their glory days and become profitable.  

How many properties are you managing? Do you manage both short-term and long-term rentals?

We currently manage around 300 properties and only do long-term rentals.

Do you work alone or with a team of property managers? Who will be my primary contact?

We are a fully staffed property management company, not a one-man show doing this as a side hustle. Our team does operate a little differently than some as we are department-based, you will be assigned a client success manager who will be your main point of contact, but unlike other companies, they are not doing all the work on your property. Some people who are good at debt collecting are not the same people that are good at leasing, or talking to plumbers so we have employees in specialized roles for all the different parts of the property management journey.

Are you purely a property manager? Or do you work as a property manager and real estate agent?

We do not actively market for new sales clients. (meaning our time is spent walking your properties and making sure rent is collected and not trying to find new clients to buy houses, that being said because of our vast network of investors and our experience as brokers. We often help our clients buy and sell investment properties.

What do you offer that sets you apart from other companies?

  1. Use of technology, from the basics of your bookkeeping being done with software and monthly reports getting sent to you, to our screening process digging through details of the applicant's bank account through Plaid, we offer more to our clients.

  2. We care about our communities, yes we work in some of the more challenging areas in Chicagoland, but our goal is to provide a fantastic experience for our tenants and create homes we would want to live in.

  3. We want to be your investment advisor and not just a babysitter, other companies collect rent, we are constantly looking for ways to make your property more successful and to help you increase your portfolio when the time is right.

How many clients do you currently have? And how long have they been with you?

About 90 owners over our properties, we are constantly adding new clients but have some clients that have been with us for 5 to 10 years.

Are you a franchise or independently owned?

Independently owned and operated

Questions To Ask a Property Manager About Fee Structure and Contract

Is your monthly management fee a flat rate or a percentage of the rent?

Flat rate of $99 per unit per month

What services are included in the monthly management fee?

The base management fee includes rent collecting, bookkeeping, a 24/7 emergency line for tenants, coordinating maintenance, and dealing with the day-to-day tenants' calls and concerns, as well as advising you on your investments.

Will you continue to charge a monthly management fee for a vacant unit?


What’s your fee for finding a new tenant?

First months rent

Do you charge a lease renewal fee?

Yes $350

How do you collect rents and when will I receive the rent payments from you?

We offer multiple ways for tenants to pay from E-check, credit card, or paying in cash at several local stores like Walgreens CVS or 7/11

Do you have a trial period?

Our contracts are month to month. If you ever think we are not living up to our end of the deal you should not be tied to a contract.

Do you have a termination clause within our contract?

Yes 30 days' notice to cancel

Do you manage properties that will compete with my property? If so, how do you equitably treat me versus another client with a competing property?

Yes, we manage many doors throughout Chicagoland, with that being said that is the reason we can get bulk discounts from our vendors to help make your investment more profitable. In terms of finding tenants we often get more hits on one property than another due to many factors but this allows us to show your property to people who may have been initially looking at a different property that got rented out by another applicant.  

What is your late rent policy? What is your late fee amount?

Chicago limits what we can charge tenants for a late fee. The formula is (rent minus $500)*.05 plus $10

Who keeps the fees that tenants pay?

We keep tenant fees. This allows us to keep our base fees low for those who do not need extra attention for misbehaving tenants but still have our fantastic staff and tools to help collect rent, serve notices, and more.

Questions To Ask a Property Manager About Legal History

Have you ever been sued by a tenant or landlord? What were the circumstances? What was the outcome?


Have you ever been accused of discrimination in your screening process?

Yes, this is why it is very important that we set and stick to our screening criteria and we do not allow owners to choose their tenants. We could quickly show that our ads, application, and all other materials clearly stated our criteria and that the tenant's credit score fell below the line.

Has the Department of Real Estate ever filed an accusation or a complaint against you or your company?



Questions To Ask a Property Manager About Homeowner Communication

How often will you send me updates about my property? How and when will you be able to talk about various problems?

You will receive monthly accounting updates in your owner's portal as well as yearly cash flow and other tax documents needed to file income taxes in January easily.  

We also will have a maintenance portal for you to get live feeds into any work orders made and dispatched out.

What do you expect from me as the owner?

We want to earn your trust and help make your investment as high paying as possible. We understand that you may not agree with every decision we make but please know that we make decisions based on research and years of experience. This is from the color we paint your apartment to what work orders we do and don’t do for a tenant. it may seem like it's not a big deal but having the most popular paint tone will help us rent your apartment faster than your preference. On the work order side, some things you may not want to pay for or think it doesn’t need to be fixed but keeping the tenant happy by spending $200 is much easier to swallow than spending $10,000 on a turn if they leave.

What’s your turnaround time on phone calls, texts, and emails received from owners?

By the next business day, often we will get back to you asap that day but sometimes we do get backed up, or are in the field.

Do you have a policy regarding landlords directly contacting tenants? Do you provide the owner’s information to the tenant?

We do not allow our owners to contact tenants and do not provide info to our owners. This allows tenants to play good cop or bad cop and say she said he said, it also means that you can become liable for things you may have never said by them saying the owner contacted me and promised x when I moved in. By not having contact you do not have to worry about being liable for anything with the tenants' issues.

Questions To Ask the Property Manager About Leases and Tenant Screening

Walk me through the rental criteria you use for screening tenants. Who decides to accept or deny a tenant?

We always require 3 times the rent for the tenant's income, as for credit we auto-deny applicants with past evictions, or any utilities or apartments in collections. In terms of scores we will rate your property between A and D Class and your credit criteria will be assigned from there. A is 650 or higher D is 500 or higher.

How long does it take you to approve tenants and have a lease signed?

From when they apply generally 24hrs but some tenants take longer to sign in using the computer than others.

Can you provide me with a copy of your standard lease agreement?


How do you handle the security deposit?

Due to the many issues with security deposits and Chicago’s RLTO, we only accept move-in fees.

Do you offer “sight unseen” leases? If yes, do you have a special addendum? We do not

Are you familiar with the Fair Housing Act? What are some common mistakes regarding these laws? Yes if you are approving tenants without strict white and black criteria it is very easy to fall into fair housing violations even if you don’t think you are.

Can you walk me through the eviction process? How many tenants have you evicted in the last year?  

First, we try everything not to evict, payment plans, offer tenants to move out on their own, offer cash for keys. But if it gets to the point of eviction we will assign your case to an attorney who will process it. This process averages between 8 to 10 months.

Is an eviction part of the cost, or is it extra?


With court costs attorney fees and notice fees evictions run between $1400 and $2000


Questions To Ask a Property Manager About Their Background


What is your personal definition of “rent-ready”? And how long does it take you to “turn” a vacant property so it’s rent-ready?

The walls were smoothly painted with no holes, all sinks and tubs were caulked, all mechanics, appliances, and fixtures working as intended by the manufacturer, locks were changed, and deep cleaned.   Once we get approval for the turn price a turn can take as little as a day to as much as a complete gut taking 30 days.

Is the lease automatically renewable? What is your renewal policy?

If you do not want us to offer a renewal to a tenant you must inform us in writing within 5 months of the lease expiration date.

How much move-out notice do you require? Do you do a pre-inspection before the tenant’s move-out? 30-day notice for a tenant to move out. We inspect once they move out.

Do you show the house while the current tenant is in the home?

Since Covid we no longer do. We realized we get better quality tenants and fewer complaints from new tenants when they have seen the fully turned unit before applying.

How quickly do you fill vacancies between tenants?

Generally 30 days from move out to move in

What is your schedule for payments when installing a tenant?


Before moving in the tenant will pay an entire month of rent and their move-in fee.

Do you have a termination clause if the unit isn’t rented after so many months?

Our agreements are all month to month if you are unhappy at any time you can give a 30-day notice and end the agreement.

Do I pay any fees when the place is empty?

As long as the turn is approved and we are allowed to find a new tenant there is no charge til the tenant moves in.

What is your philosophy on tenant selection and getting properties rented?

We want solid tenants over getting tenants quickly I will not compromise are requirements to get a tenant in an apartment a few weeks early.  

Do you take photos of the property before and after the move-in and move-out?


Do you offer a tenant placement guarantee?

We will re-rent your unit for free if the tenant does not stay for at least six months.

What lease lengths do you offer? Do you charge extra for month-to-month leases?

We offer 1 yr leases, if a tenant stays past that without signing a new one-year lease there is an extra charge to their rent.

Do you do a breakout clause?

We allow tenants to pay 60 days of rent beyond their last day to break their lease this gives us two months to find a new tenant and not lose any income for you.

Do you have a rental deductible?

We do not in the City of Chicago it would be very hard to get this to work,

Do you have lease language that requires tenants to pay for the damage they cause that’s not wear-and-tear?


We do.

Questions To Ask a Property Manager About Maintenance and Tenant Relations

How often do you inspect the properties you manage?

We inspect all units before renewing, we also have eyes on the properties when we do things like common area cleans, or maintenance calls.

Do you require tenants to have renter’s insurance?

We do not as it is almost impossible to track. We also find often owners think this covers more than it does. It mainly covers their possessions in the case of theft or damage.

Who keeps the damage deposits?

We do not use them in Chicago.

When do you return the security deposit? Do you get approval from the landlord first?

We do move-in fees, not security deposits.

What is your personal philosophy on deferred maintenance?

Get it done. Spend a nickel and save dimes, deferring maintenance only makes the maintenance.

Who do you use for electrical, plumbing, and appliance repairs?

We have a Rolodex of vendors as well as an in-house maintenance team.

Do you do “as is” appliances?

No Chicago does not allow this if you supply it you must fix it.

Who pays for pest control?

Owners do in Chicago for multifamily homes, and single-family homes if you can prove tenants caused pests we can charge them back.

Is your maintenance in-house or a vendor? How do you interview your contractors? Are they licensed and insured?

Most of our vendors are referred to us by trusted clients or other vendors. Anyone that goes onto your property is licensed and insured for whatever reason they are on your property for.

What’s your standard dollar amount threshold for owner involvement? And will you send me photos (before and after repairs) and invoices?


$1000 unless the work is needed. Yes, you will get photos and invoices.

What is your philosophy on repairs and replacement?

Depending on the situation a year old water heater we would want to repair it if the fix is $100, if the unit is 18 yrs old we would want to replace it.

Do you charge a markup or coordination fee on the work your contractors complete?


Because we do maintenance in-house we have to charge enough to cover not only the labor and supply but things like insurance and overhead so yes there is profit made on our maintenance, but this also allows us to charge much less than other vendors of similar quality of work.

What is the best way for tenants to reach out to you regarding an issue? And what’s your time frame for responding?

 Our office number is 224-601-5415 we also have an online portal for maintenance requests. Our emergency line is open 24/7 for tenants to call into.

What do you consider emergencies? How do you handle off-hour emergencies?


If left til the next business day will it cause damage to the property or the health of the tenant? If so we dispatch right away.

How do you handle tenant calls for repairs? Do you troubleshoot with your tenants first?

 Absolutely, The goal is always not to send someone out when possible.

Do you use any online programs or software to streamline your operations? 

Yes for maintenance we use property meld which gives you a portal to see work orders as they come in.

Questions To Ask the Property Manager About Their Strategy on Marketing

How would you market my property? Can you show me an example of one of your property listings?


You can click on our website to see all of our listings. We use syndication services to go to hundreds of websites.

Will you advertise and show a property while it’s occupied, or do you insist on properties being vacant before you advertise them?


Vacant first we noticed a much better experience for all this way.

How do you determine when to raise the rent?

When the lease is coming up for renewal we will run comps and estimate turn costs and vacancy costs to weigh the increase.

Do you perform a market evaluation for every renewal?

We do.

How are market rents calculated? What are your rental rates based on?

Comparable rent from around the area.

When do you recommend lowering the rent to fill a vacancy?

When we go a week without a showing or two weeks without an application

If I find a potential deal, are you willing to analyze the property to determine its curb appeal and potential rental price?


Our team has a background as realtors and investors to help show you if a property is a good deal or a scam.

Got more questions for us email us at or give us a call 224-601-5415