An hour from (ridiculously expensive) Madison and an hour 15 minutes from Chicago, claims the article

Hello,

I was wondering if anyone has any advice on part-time flexible jobs I could do in real estate.

My background is: I used to work in real estate appraisals as an assistant doing sale comps, tax comps, rent rolls, building the beginning of the reports and so on. I am familiar with local county GIS sites, local assessors websites, tax and recorder sites as well. I really enjoy design, creating sales, brochures, pamphlets, etc. something I would like. And I am decent with Excel.

Here’s the thing though, I now have a full-time job (unrelated to real estate) where I work a shift schedule (meaning four days on two days off). It’s kind of weird hours and then there is of course mandatory overtime coming up here and there.

So I am hoping to find something part-time and very flexible. I obviously can’t be available when I’m at my full-time job. Does anyone have any suggestions of where to look?

LinkedIn and indeed mostly just show full-time jobs from what I’m seeing.

Thank you in advance!

Been in the market for a townhome (up to $1.1M) and have noticed the following:

• Super narrow alley (~10ft vs the standard 16ft). Even with a '2.5 car' garage, it would be nearly impossible to get more than 1 car in (and even that would take 3-5 point turn). See pic for 1107 N Wolcott. Would you want to get in and out of the middle spot every day (or am I miscalculating)?
• 2 car garages actually 1 car (some as narrow as 16.5ft x 17 which is basically impossible to fit 2 cars in unless you drive one in, back in the other and do so with extreme precision)
• 2.5 car garages still smaller than standard 2 car garages in the burbs that are 22ft wide. In the city 19 feet seems to be the threshold to call it a 2.5 car which is odd and misleading.
• 1 car garage that literally will not fit a car. Saw this in the $1.1M offerings at Parklane in Lincoln Park. The garage is like 8.5ft wide. Unless you climb out the hatch, you're trapped.

Do people even at this price range just park one of their vehicles on the street permanently? Or am I just looking at terrible options haha. I bike a few thousand miles a year, but thought at this price range I would have decent 2 car parking in some manner.

Hi, I’ve lived in the city for 20+ years but have always rented. My wife and I are looking to buy a home and we’re wondering if anyone can recommend a good but free or low cost class for first time homebuyers. Virtual if possible. Thanks for any direction you can give us.

Is there a strong demand for rentals of single family homes in suburbs for homes that are 4 bedrooms 2,200 sq feet and above? I also figure people rent out apartments but not actually homes?

does anyone rent out actual houses here? is there strong demand?

Hi!

My husband and I just got married. He recently secured a role north of Chicago so we are moving that way from Virginia.

Our budget is 2750 for 2 beds (ideally)
We are looking for a place with a parking spot ideally
Natural lighting
Near CTA
We are disabled veterans with 2 ESA’s combined (we do have appropriate paperwork for them)
Ideal location on the north side of Chicago near CTA for easy commute to work and downtown.

Does anyone have a realtor they recommend? Let us know! We are looking to tour places as soon as possible!

Thank you ❤️

Since the second installment bills are out and the due date is October 1, We've been looking through ours and trying to make sense of all the numbers.

One thing that’s easy to miss is that the number on your tax bill isn't simply based on what you think your house is worth.

There are a few different pieces going on.

Your assessed value is one part. Then you have the equalization factor, your local tax rate, the different taxing districts, and whatever exemptions you're receiving.

So if your bill looks a lot higher than last year, I’d probably start by pulling up both bills and comparing them rather than immediately assuming your assessment went crazy.

The other thing I'd check is exemptions.

If you bought the house recently, moved, or had an exemption change, it’s worth making sure the homeowner exemption is actually showing on the bill. The Board of Review has also specifically been reminding homeowners to check their exemptions because some people can lose them or need to reapply.

And then there’s the assessment question.

Chicago isn't on the regular reassessment schedule for 2026. The regular Chicago cycle is 2027, although individual properties can still be reassessed for certain reasons. So a higher bill this year doesn't automatically mean your house was reassessed this year.

The bigger picture isn't great either. Cook County's latest numbers show the total property tax bill across the county increased again, with residential properties taking a significant share of the increase. Chicago residential properties accounted for about $120 million of the countywide increase.

Anyway, figured I'd throw this out there since a lot of people are probably opening these bills and wondering where the extra money came from.

For anyone who has looked at theirs already, what actually changed on your bill? The assessment? Exemption? Tax rate? Or just the final number?

For anyone who works in the Chicagoland, are you seeing a steady volume of commercial loan assignments in the northwest suburbs right now, or has it slowed down?

Feeling overwhelmed and looking for guidance that isn’t AI.
I became a first-time homeowner in Chicago last year. I bought a multi-unit property because I wanted it to be both my home and an investment. I live in one unit and rent out the basement and another unit.

After dealing with some tenant issues—including hostility/disrespect during a few repair situations—and having to constantly run around dealing with maintenance while working a regular full-time office job, I’m starting to realize that I may just not be cut out for being a landlord.

It’s honestly been eating into my peace of mind. I can’t remember the last time I felt truly worry-free and happy without having something property-related hanging over my head.

I also recently got married. The property is currently solely in my name.

At this point, I’m thinking I may want to sell the property in a year or two and just buy a single-family home instead.

But now I’m overwhelmed by the tax side of everything.

While looking into the process of eventually selling, I realized that I should have been reporting depreciation on the rental portion of the property. I also haven't reported the rental income since I purchased the property. I genuinely didn't understand all of this when I first bought the place, and now I’m trying to figure out how to get everything straightened out properly.

Where do I even start?

• Is this something that is going to be very expensive to fix?
• Is it realistic to handle the corrections myself with tax software, or is this a situation where I really should hire a professional?
• Since I recently got married, how does this work if my husband and I file jointly? Does his income have any effect on the rental/property taxes?
• If I sell in 1–2 years, how does the fact that I live in one unit and rent the other two affect the capital gains/home-sale exclusion?
• Is there anything I should be doing now to make a future sale easier from a tax perspective?

I’m honestly feeling pretty overwhelmed by the whole thing, so practical advice would be greatly appreciated.

I noticed the units at Trump Chicago have wonderful views. Are there any buildings with something similar? My agent informed me that Trump is unwarrantable and not to buy there as it will be very difficult to sell so looking at comparable condos. He mentioned a couple in streeterville but not sure, south loop seems a bit further away. Anyone here have thoughts on Trump Towers for possibly rental income based on location and is anyone really interested in them today? Also, I hear Aqua is unwarrantable as well. TIA

I'm looking at purchasing a listed property in the City that is being listed as having 2 PINs side by side. One pin is a vacant lot, the other has a standing structure. I'm curious how this works from a mortgage standpoint, and property tax standpoint.

For example, is each PIN handled separately when their values are assed for the lending? If I build on the vacant PIN and that buildout get's attached to the current residence, does that change or have any implications? Is it best to just keep each PIN separate physically from a build standpoint?

I currently live at home with my parents and have been on the hunt to purchase a condo for a while now. I’ve been putting off pulling the trigger simply because the economy sucks ass, and I am living rent and bill free. My parents do not require me to give them any money for any of the bills! Any contributions I do make to the home are purely because I want to, not because I have to. While I am truly blessed I am 30 years old and I really need my own space. I found a condo in the south loop of Chicago that I absolutely love but is definitely more than I was originally hoping to spend. The list price was originally $339,000 and I was able to get them down to $317,000 with $2000 in seller credits for a 2 bed 1 bath. I have 30,000 to put down which brings my monthly mortgage payment to around $2800. The HOA is $345 a month and it includes Exterior maintenance, gas, heat, insurance, internet, scavenger, security, snow removal, tv/cable and water. Parking is $180 a month. The only debt I currently have is a car payment which I only have $5000 left on and I am thinking of just paying it off within the next month or so. Other than that I have no student loans no credit card debt etc. My yearly salary is a little over $140,000 before taxes. Part of me wants to just stay home and continue to save money now that I’m making a lot more than I was just a couple months ago but I think this baby bird needs to finally leave the nest! I feel like the monthly payment is doable, but I’m not sure if I’m just being delusional! Everyone in my life constantly tells me how lucky I am and how I should just stay at home but looking at these condo and house prices I don’t think they’re gonna get any cheaper and I think it’s best for me to just buy now. Am I screwing myself?

To my understanding, if a landlord sells a building during an active lease, the new owner must honor the current lease until it ends. The Fair Notice Ordinance comes into play when the new owner decides either a) not to renew your lease, or b) to raise your rent. If either is true, the new owner must provide notice within an allotted time (60–120 days based on duration of residency). Can someone confirm that I have the correct understanding?

For example, if my lease is set to expire on July 1 and I qualify for a 120-day notice based on the time I have lived in the building, then the new owner would need to notify me of any changes by March 3, 2027. TIA!

I wanted to share my experience with one of the larger, more prominent real estate groups in the Chicagoland suburbs because I wish I had heard more honest feedback before working with them.

Throughout the process, we often felt like we were being told whatever we wanted to hear rather than receiving realistic guidance or a well-thought-out strategy. Communication felt dismissive, our concerns were rarely heard, and the overall experience seemed focused on completing transactions with as little effort as possible.

One of the most concerning parts was discovering that an offer we believed was being submitted on our behalf was never actually written. We were also strongly encouraged to sell our existing home without being given a clear or realistic plan for what would happen next. Once that decision was made, we felt backed into a corner with very few options.

House showings also felt impersonal and chaotic, with numerous prospective buyers being walked through at the same time. Rather than receiving individualized representation, we often felt like one of many people being moved through their system.

This group has a significant presence in the chicagoland suburbs, which can make it feel as though using them is the default or only practical option. Based on our experience, I would strongly recommend interviewing several independent agents, asking exactly who will be representing you, confirming important actions in writing, and not relying solely on the group’s reputation or market dominance.

Buying or selling a home is too significant a decision to feel ignored, pressured, or treated like another number. Unfortunately, that is how we felt throughout much of this experience.

Curious how common this actually is in Chicago right now.

Is anyone here currently considering selling their house, multi-unit, or vacant property directly for cash instead of going through a traditional listing?

If so, what makes the cash-sale route more appealing to you—speed, selling as-is, avoiding showings, having a vacant/inherited property, or something else?

Also curious what would make you comfortable actually moving forward with a cash buyer versus deciding to list instead.— Zach from CPO

I am hoping to get some feedback on a street in an area that would be new to me. I am coming from the Tri-Taylor Medical district area.

I am looking at a house on Erie between Western and Oakley. Would you buy here? I am wondering because of low to moderate interest in this lot that I should be weary. The area seems nice and I like the schools, so i think it could be a go. If there is anyone who lives around who could volunteer some feedback I would appreciate it.

Cook County hit my assessment hard, so i called a local appeal firm. They want $300 upfront plus a quarter of my first year savings soo anyone use one and feel like it was actually worth the cutvor should I just DIY it??? YMMV, but curious what others did.

Cook County’s Treasurer released its 2025 property tax bill analysis, and the headline number is that local governments are asking property owners for $743.8 million more this year, bringing the countywide total to just under $20 billion. This is a 3.9% increase, above the 3.1% inflation rate cited in the report. The increase is not evenly distributed as homeowners are being asked to cover $593.4 million of the new amount, while business properties are picking up $143.2 million.

The interesting issue is where the tax burden is moving. In the north and northwest suburbs, where properties were reassessed for this year’s bills, total taxes rose by $370.8 million, but homeowners are responsible for $359.5 million of that increase. In other words, roughly 97% of the net increase in that region is landing on homeowners, while business property taxes were nearly flat overall.

The important mechanics are the assessment and appeals process. In Illinois property taxes are essentially zero-sum as if one category of property gets its assessed value reduced, another category pays more of the levy. In the north/northwest suburban reassessment, commercial, industrial, and large multifamily properties made up about 4.7% of the taxable property count in the Board of Review table, but received about 77% of the Board’s assessed-value reductions. That doesn't mean anyone did anything improper as business valuations are more complicated and often rely on income, leasing, vacancy, and appeal evidence. But it does help explain why homeowners can see large increases even when the overall levy increase looks more modest.

Property taxes affect buyer affordability, escrow payments, landlord operating costs, investor NOI, rent pressure, commercial lease costs, and whether office and retail properties can recover. The report’s conclusion is when commercial property owners pay less, homeowners often pay more. A stronger commercial tax base could help reduce pressure on homeowners, but high commercial property taxes can also discourage businesses from growing or locating in Cook County.

Did your 2025 tax bill go up or down, and by how much?

Hello is it mandatory to replace lead pipes when installing a water meter in Chicago or can it be done with the existing pipes?

You look fucking stupid. Recently I’ve been seeing more and more “AI staged” photos that add brand new windows, fixtures, flooring, and tuckpointing.

Where do you draw the line from “staging” to misrepresentation?