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231 North Pine Avenue, Chicago, IL, USA
Priced too high to cash-flow with a loan — an equity or tax play, not income.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$52,682
$4,390/mo · at 52% occupancy & $371/night
-$555
-$46/mo after costs & mortgage
Cap rate
5.9%
Cash-on-cash
-0.4%
DSCR
0.98
Confidence
Your assumptions
Revenue
$52,682/yr
Market avg: $52,682/yr · 52% occ · $371 ADR
Financing
$29,939/yr
Operating costs
$23,299/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 29 properties
$193–$679
Median $371
27%–88%
Median 52%
$28.5K–$84.9K
Median $51.2K
132–365
Median 290
This property · $52.7K
Comparable properties (29)
Cash flow potential Medium · Appreciation potential Medium
204 days available · 128 days booked ·
284 days available · 127 days booked ·
365 days available · 220 days booked ·
322 days available · 159 days booked ·
278 days available · 182 days booked ·
349 days available · 176 days booked ·
300 days available · 148 days booked ·
358 days available · 136 days booked ·
266 days available · 119 days booked ·
365 days available · 214 days booked ·
316 days available · 156 days booked ·
247 days available · 117 days booked ·
265 days available · 190 days booked ·
352 days available · 143 days booked ·
247 days available · 190 days booked ·
318 days available · 117 days booked ·
284 days available · 154 days booked ·
240 days available · 113 days booked ·
290 days available · 138 days booked ·
302 days available · 97 days booked ·
276 days available · 145 days booked ·
324 days available · 119 days booked ·
132 days available · 119 days booked ·
262 days available · 128 days booked ·
279 days available · 123 days booked ·
235 days available · 103 days booked ·
304 days available · 128 days booked ·
322 days available · 97 days booked ·
315 days available · 151 days booked ·
Revenue and occupancy reflect Chalet's modeled estimates from observed booking activity for comparable active listings. Individual results vary with management, seasonality, and pricing.
Who this property is for
The same property is a great buy for one investor and a trap for another. Here's the honest read.
1031 / high-equity buyer
~$123.5K
Year-1 tax shield
Buying with cash or low leverage removes the debt-coverage problem entirely, so the thesis rests on appreciation plus a large first-year write-off. At roughly 25% of purchase price, the shield is substantial enough to carry the deal on its own.
Price-disciplined buyer
$490.7K
Break-even purchase price
Break-even sits only ~2% below the Zestimate, which is inside normal negotiating range. A disciplined buyer has a realistic path to making this work at close to asking.
DSCR cash-flow buyer
0.98
DSCR at asking
At asking price the property doesn't cover its own debt service, so it won't qualify for DSCR financing as modeled. If you need cash flow from day one, look at a mid-term-rental fallback or a different Chicago submarket.
For a buyer who materially participates and qualifies for the STR tax treatment.
$123.5K
Estimated first-year deduction · range $102.5K–$140.8K
Why this matters here
At a marginal bracket, this deduction can be worth $37.9K–$52.1K in estimated federal tax saved.
This only applies if you meet the IRS material-participation tests for short-term rentals and are not using a full-service property manager.
Estimate, subject to CPA review. Cost-segregation percentages shown here are illustrative and depend on an actual study of the property.
Some states do not conform to federal bonus depreciation, so your state may not allow the same first-year treatment shown above.
Chalet can introduce a cost-segregation partner — this is not tax, legal, or financial advice.
How cash-on-cash return moves with purchase price. The marked line is break-even (1.0 DSCR).
At this price: cash-on-cash -0.4%, DSCR 0.98, cash flow -$555/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | 5.9% | 1.31 | Positive |
| -22% | $390,000 | 5.0% | 1.26 | Positive |
| -15% | $425,000 | 3.0% | 1.15 | Positive |
| -8% | $460,000 | 1.3% | 1.07 | Positive |
| Asking | $500,000 | -0.4% | 0.98 | At break-even |
| +8% | $540,000 | -1.8% | 0.91 | Below break-even |
| +15% | $575,000 | -3.0% | 0.85 | Below break-even |
Break-even price
$490,726
~2% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$9,274
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$4,388/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $4,390 · peaks at $5,586 in Apr
Annual avg 51% · peaks at 65% in Aug
−$46/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:16.9%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.98 · lenders typically require 1.0+.
Get matched with 2–3 vetted STR lenders, free.
What the deal returns over the hold — including the tax shield, which is the whole point for an appreciation buyer.
Levered IRR
18.8%
over 5-yr hold, with tax shield
Equity multiple
2.1×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+7.1 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $45,140 | $198,949 |
| Year 2 | $132,894 | $51,250 | $45,375 | $229,519 |
| Year 3 | $137,274 | $78,813 | $46,413 | $262,499 |
| Year 4 | $141,970 | $107,753 | $48,264 | $297,988 |
| Year 5 | $147,007 | $138,141 | $50,942 | $336,089 |
Projection, not a promise.
Assumes 5.0% annual appreciation, 1.5% rent growth (operating costs held flat), and that the property qualifies for short-term-rental tax treatment. The year-1 depreciation shield depends on a real cost-segregation study and your tax situation — consult a CPA.
Appreciation is the dominant driver of this return. When cash flow is negative, the deal depends on the property gaining value — it is not paying for itself from income.
Appreciation, rent growth, and financing rates are editable under Edit financials.
STR deals turn on local rules and demand that a generalist agent misses. Chalet matches you with a vetted Chicago agent who knows which properties actually cash flow — and which to avoid.
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Disclaimer
This page and the data presented are for informational purposes only. The information provided should not be construed as financial, legal, or investment advice. Market conditions can change rapidly, and past performance does not guarantee future results. Always consult with qualified professionals before making investment decisions.