Pilsen vs. Avondale 3-Unit – Which Is the Smarter Play for a House Hack?

Question

Hey everyone,

I’m comparing two 3-unit multifamily properties in Chicago and could use some input from local investors or anyone who’s done a house hack recently.

• Option 1 – Pilsen: Asking around $750K, recently updated, with below-market rents. Taxes are about $8,000/year, but it hasn’t been reassessed yet — so I’m concerned they could jump significantly once the sale closes.
• Option 2 – Avondale: Similar price range, but the building is older and needs some updating (kitchen, bath, paint, etc.). Taxes are already around $13,000/year, so they seem more “stabilized” from a reassessment standpoint.

Option 1 – Pilsen: Asking around $750K, recently updated, with below-market rents. Taxes are about $8,000/year, but it hasn’t been reassessed yet — so I’m concerned they could jump significantly once the sale closes.

Option 2 – Avondale: Similar price range, but the building is older and needs some updating (kitchen, bath, paint, etc.). Taxes are already around $13,000/year, so they seem more “stabilized” from a reassessment standpoint.

My realtor is recommending Pilsen, citing stronger appreciation potential and rental demand. But my worry is that after reassessment and tax hikes, it may be tough to break even once I move out and rent my own unit in a couple of years.

For those familiar with these neighborhoods or Cook County taxes:

• Have you seen big post-sale tax jumps in Pilsen recently?
• Would you lean toward Avondale for longer-term stability, even if it needs more work upfront?
• Which area makes more sense for a first house hack with plans to refinance or buy another multifamily in 1–2 years?

Have you seen big post-sale tax jumps in Pilsen recently?

Would you lean toward Avondale for longer-term stability, even if it needs more work upfront?

Which area makes more sense for a first house hack with plans to refinance or buy another multifamily in 1–2 years?

Appreciate any insights from people who’ve run the numbers or invested in these markets!

Tj Floros · Answer

Your agent should prepare a pro forma that models the building’s worst-case operating scenario, specifically assuming property taxes are reassessed to reflect the purchase price.

For example, if the building is currently assessed at $250K and taxes are about $8K per year, but you’re buying it for $750K, then it’s realistic that the county could reassess it closer to that new value with taxes 2x'ing or 3x'ing. Run the numbers assuming that higher tax basis, and if the deal still pencils out under those conditions, then you can move forward confidently with whichever option makes the most sense.

A purchase itself will not trigger a reassessment in Cook County. However, every property is automatically reassessed once every three years, and that process is now almost entirely handled by a computer algorithm that looks at factors like recent sale prices (especially if the property sold on the open market), neighborhood trends, and comparable assessments.

The only time a human assessor actually reviews your valuation is if you file an appeal. For that reason, I always recommend clients either learn how to appeal themselves or hire a good property-tax attorney who specializes in Cook County appeals. It can make a big difference in keeping your tax bill reasonable.

Paul is right about the north side data, but every situation and deal is different for each investor.

Matt F. · Answer

Impossible to assess without outlining income potential

Jarret Jarvis · Answer

Hey Rochelle, great question and solid comparison. I’m a Chicago investor and agent who’s worked with a lot of house hackers in both neighborhoods, so here’s how I’d think about it:

1. Tax risk (Pilsen):
You’re right to be cautious. In Pilsen, reassessments have been pretty aggressive the past couple of years, it’s not unusual to see 25–40% jumps post-sale depending on how far below-market the current assessment is. The county assessor now tracks sale prices closely, so they’ll likely bump yours up near the purchase price within the next cycle. If current taxes are $8K, you might realistically be looking at $11–12K once reassessed.

2. Stability vs upside:
Pilsen will likely continue to appreciate faster, proximity to downtown, 18th Street development, and strong rental demand, but that comes with volatility: higher taxes, ongoing gentrification debates, and limited long-term rental affordability.
Avondale, on the other hand, is more stable, solid tenant base, steady growth, and most properties there have already been hit with their reassessments. You’ll trade a bit of short-term equity growth for predictability and lower renovation risk once it’s updated.

3. For a first house hack:
If you want smoother cash flow and fewer surprises while learning the ropes, I’d lean Avondale. If you’re more comfortable with some short-term risk and plan to force appreciation (light reno + rent increases), Pilsen could yield a better return when you refinance in 12–24 months.

Either way, I’d run two sets of numbers, one assuming Pilsen’s taxes jump to ~$12K and one factoring in $30–50K in renos for Avondale, then compare your post-move-out cash flow side by side.

Happy to help you model both if you want to drop the rent and expense figures.

Rochelle Fernando · Answer

Inheriting tenants in two units and one empty unit for owner occupancy.

John Clark · Answer

Are you inherenting the tenants or is the pilsen building being delivered empty?

given prices and tariffs, I like the idea of a remodeled building.

Brie Schmidt · Answer

@Rochelle Fernando - I never underwrite with current taxes.  They will go up, I always assume about 80% of the purchase price for the next reassessment and then use the tax rate for the property.

For the Avondale one, is in the ordinance zone?

Paul De Luca · Answer

@Rochelle Fernando

Avondale has seen stronger price appreciation over the long run and within the past year (10.9% YoY) while Lower West Side Pilsen is -4.3% YoY. Of course that's no guarantee of future appreciation rates but something to consider.

It's difficult to say which is a better fit for you without knowing the financing terms, condition, and projected cash flow. It also depends on your willingness to do rehab or if you prefer to get something more turnkey. Run some different scenarios with estimates of the future tax amount for the Pilsen property to see if the numbers still look attractive with higher taxes.

Rental demand in both areas seems similar as well based on median & average market time but Avondale generally has higher median and average rents.

Aaron Zimmerman · Answer

I like both areas and both have strong cases for appreciation. Chicago just got reassessed in 2024, so you won't get another reassessment until 2027.

To more fully assess the situation, it'd be helpful to have the numbers in front of us with cash flow potential

Daniel K. · Answer

Hi Rochelle,

The short answer is--honestly, I don't think you can go wrong with either neighborhood. I own a three unit building in Avondale and it's been great so far, but Pilsen is also showing tremendous upside potential. Debating one over the other is splitting hairs, if you ask me. Focus on the fundamentals of each deal and let the numbers guide you. To answer each of your questions more specifically--

• Have you seen big post-sale tax jumps in Pilsen recently?
• 
• Don't worry about property tax jumps in one area over the other. They're both Chicago and taxed as the same percentage of assessed value (lately about 2.1%). Once you buy the property the assessor should peg the assessment at the sale price for the tax year in which you bought it, so the previous owner's tax situation is moot.
• 
• Would you lean toward Avondale for longer-term stability, even if it needs more work upfront?
• 
• Without much detail provided it's hard to say. Focus on the numbers (not taxes), and let that guide your decision.
• 
• Which area makes more sense for a first house hack with plans to refinance or buy another multifamily in 1–2 years?
• Honestly, either would work

Best of luck!

Pilsen vs. Avondale 3-Unit – Which Is the Smarter Play for a House Hack?

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