I own a 3 unit near Wrigley area and am potentially moving out of state. I'm considering property management companies but am hesistant to put my trust into a company. I have a lot of contractors that I trust, and am hoping I'd have a say in some of the contractors I use for more serious repair projects. Any recommendations for companies and/or individuals? Are there different levels of property management if I still wanted to have control over some aspects of management?
Real Estate Broker · Lincoln, NE · Member since 2026 · 64 posts · 12 votes
4mo
If you’re moving out of state, it’s completely normal to feel hesitant about handing things over to a PM company — especially when you already have contractors you trust. You’re definitely not alone there; a lot of owners in Chicago ask the same thing when they relocate.
On your question about control: yes, most management companies offer different levels of service, and many will let you keep your preferred contractors for bigger repairs. The poster specifically mentioned wanting “a say in some of the contractors I use for more serious repair projects” , and that’s something a good PM should be able to accommodate.
A few things I’d look for when interviewing PMs in Chicago:
Whether they allow owner‑approved vendors for major work.
How they handle communication and repair approvals when you’re out of state.
Whether they offer tiered service so you can stay hands‑on with certain decisions.
Their process for inspections, rent collection, and tenant communication.
A hybrid setup often works well: you keep strategic control and your trusted contractors for bigger jobs, while the PM handles day‑to‑day issues, emergencies, and tenant coordination.
If you want, I can help you draft a shortlist of Chicago PMs that fit what you’re looking for or put together a quick interview checklist.
Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
4mo
Hey There @Milo Keranen - I totally understand where you are coming from. I feel the exact same way.
I'd consider looking into www.hemlane.com - they are like the perfect hybrid between self-management and having a PM. Through their maintenance portal, you can upload your own vendors to have them communicate with the tenants.
If you were in a different area of Chicago, it may not be the best fit, but I genuinely think that it will be perfect....if that doesn't work then move to a PM.
I own a 3 unit near Wrigley area and am potentially moving out of state. I'm considering property management companies but am hesistant to put my trust into a company. I have a lot of contractors that I trust, and am hoping I'd have a say in some of the contractors I use for more serious repair projects. Any recommendations for companies and/or individuals? Are there different levels of property management if I still wanted to have control over some aspects of management?
We’re a Property Management Company (PMC) in Metro Detroit ONLY, with 25+ years of experience, and we’ve seen owners make the same mistakes, over & over again when looking to hire a PMC – which drives us nuts!.
In our experience, the #1 mistake owners make is ASSUMING all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY.
So, owners mistakenly think price is the only differentiator – and look for a PMC like they’d shop for groceries☹
We encourage you to learn from the mistakes of others by reading posts here on BiggerPockets from owners that picked a PMC solely by price and regretted it.
We recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.
Even if someone gives you a referral, do NOT make the mistake of assuming that just because a PMC met their expectations, they’ll meet your expectations. We all have our own expectations and what works for someone else, may not work for you.
If you’re new to all of this, it's often a case of not doing enough research, as you don't know what you don't know!
So, ask more questions!
EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean? What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.? You’d be shocked by how little actual screening many PMC’s do!
This also leads owners to ASSUME simpler is better when it comes to management contracts.
The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!
A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings. Why do you think purchase contracts are so long and have such small print?
We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.
EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!
P.S. If you just hire the cheapest or first PMC you speak with and it turns into a bad experience, please don’t assume ALL PMC’s are bad and start trashing PMC’s in general. Take ownership of your mistake and learn to do the proper due diligence recommended above😊
Here’s some articles we’ve contributed to BiggerPockets about screening a PMC BETTER than you would a tenant!
Property Manager · Chicago, IL · Member since 2026 · 40 posts · 33 votes
4mo
Honestly I think your concerns are completely valid. A lot of owners worry that handing over management means losing control of their property or being forced into using vendors they don’t trust. In my opinion, the best management relationships are collaborative. We manage properties ourselves at The Boutique Home Group and many of our owners still like to have input on larger repairs, contractor selection, or capital improvement projects. There are definitely different levels of management depending on how hands-on you want to remain.
I also know the Chicago market extremely well — especially neighborhoods around Wrigley/Lakeview — and understand the challenges that come with managing older multifamily buildings remotely. Feel free to drop me a message or email sometime if you want to chat or grab a coffee locally. Happy to give you some honest advice even if you don’t end up working with us. We are based on the NW side in Sauganash for those that know this little corner of Chicago.
Real Estate Agent · Memphis · Member since 2026 · 541 posts · 315 votes
4mo
I’ve found there’s definitely a middle ground between fully handing everything over and fully self-managing. A lot of owners still keep control over larger repair decisions, contractor relationships, or approvals while letting the PM handle leasing, tenant communication, collections, and day-to-day coordination.
Personally, I’d want clarity upfront on how flexible they are with owner involvement. Some PMs prefer using only their own vendors, while others are more collaborative if you already have contractors you trust. For me, the biggest thing is transparency and process — I want to know exactly how maintenance approvals, communication, and vendor coordination are handled before turning anything over.
I own a 3 unit near Wrigley area and am potentially moving out of state. I'm considering property management companies but am hesistant to put my trust into a company. I have a lot of contractors that I trust, and am hoping I'd have a say in some of the contractors I use for more serious repair projects. Any recommendations for companies and/or individuals? Are there different levels of property management if I still wanted to have control over some aspects of management?
Hey Milo, totally reasonable concern. A lot of owners use property managers for the day-to-day stuff but still keep control over bigger decisions and preferred vendors. Most decent PM companies will let you use your own contractors for larger repairs or at least give you the option to approve bids before work gets done, especially if you already have trusted people. There are definitely different “levels” of management too. Some are full service where they handle everything, while others are more hybrid where they do leasing, rent collection, tenant communication, etc. but loop you in on maintenance decisions above a certain dollar amount. I’d just make sure whatever agreement you sign clearly outlines spending limits, contractor approval rights, and communication expectations. One thing I’ve seen help a lot is starting with a shorter contract term first so you can test how responsive and transparent they are before fully handing over the keys. Also ask how they handle emergencies, vacancy turnover, and whether they upcharge maintenance work since that’s where some PMs make extra money.
These are all valid concerns. My husband owns a property management business in Chicago, and half of his clients are out of state owners. You can learn more about his business here!
Real Estate Broker · 3412 S. Harlem Avenue Riverside, IL 60546 · Member since 2015 · 6k+ posts · 5k+ votes
4mo
@Milo Keranen in terms of property management companies, GC Realty is a great option. Mark runs the Straight Up Chicago Investor's podcast which is a huge part of our local network here.
I think the big thing when looking at whether to self-manage or hire is how long this out of state move will last and what your business plan is with the property. Is this a forever hold? Will you ever come back and get personal use out of the building? A lot of times I have found that investors that start with the end in mind get more clarity and are able to answer the immediate tactical questions like "do I want to hire a PM".
If you are never planning to come back, 100% you want a PM. The self-managing route will go fine.... until it doesn't. That is how property management is. It's easy except for all the hard parts!
I own a 3 unit near Wrigley area and am potentially moving out of state. I'm considering property management companies but am hesistant to put my trust into a company. I have a lot of contractors that I trust, and am hoping I'd have a say in some of the contractors I use for more serious repair projects. Any recommendations for companies and/or individuals? Are there different levels of property management if I still wanted to have control over some aspects of management?
You definitely don’t have to give up full control to use property management.
A lot of owners use different levels of management depending on how involved they still want to be. For example:
Tenant placement only
Rent collection only
Full-service management
Maintenance coordination only
Hybrid setup where you keep your own contractors but the PM handles tenants/emergencies
Since you already have contractors you trust, I’d specifically look for a PM company that allows owner-approved vendors and lets you set repair approval limits.
For a 3-unit near Wrigley, there should be several Chicago PM companies that offer flexible structures instead of fully taking over operations.
I’d also ask:
Do they mark up repairs?
Can you approve larger expenses first?
Do they do periodic inspections?
How responsive are they with out-of-state owners?
Moving out of state is usually where having at least partial management starts becoming worth it.
Property Manager · Fort Worth, TX · Member since 2014 · 77 posts · 29 votes
4mo
That hesitation is healthy. A good property manager should not make you feel like you handed over the keys and lost visibility. The best setup is usually clear spending limits, written approval rules, and honest communication before repairs happen...especially if you already have contractors you trust. I’d ask every PM how they handle maintenance markups, vendor choice, and owner approvals before I looked at price. Cheap management gets expensive fast when the process is muddy.
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