Is this a method people are using to offset the expenses, or is negative cash flow expected until you acquire the property and raise rents to achieve the desired ROI?

Highest return should be the goal.Lower LTV to achieve cash flow is paying for the cash flow upfront and greatly reduces the return.  

Duplex sold in 2025 for mid $500’s3 bed/ 1 bath units; approx 2000 sqft Well maintained/good shape Price per unit is approx $270k/unit and $260/sqft  Higher than what we’ve evaluated out of Exeter, but this is also 3 bedrooms each unit.  

I can achieve this goal by doing a cash-out refi and ballooning my HELOC balance but my new rate would be 6.625%, a decent improvement from 7.35%.

Due to DSCR loan limits, we likely won't achieve a "perfect refinance" and pull out all our (well, my) equity, and likely leave 30-40k of my equity trapped.The Conflict:If we stick to a straight 50/50 ownership split:Him: $0 invested = Infinite Cash-on-Cash Return.Me: $30k invested = ~5% Cash-on-Cash Return (based on remaining cash flow after reserves).This feels imbalanced to me.

In Chicago they made it illegal to do STR for a single family, condo or 2-4 unit unless claim it is owner occupied with the only required proof needed being ¨unit is the home address on your ID¨ so many people are able to to sneak around the rule.

Initially you need to get a copy of the current Rent Roll, delinquency report, and Security Deposit status; (request estoppel certificates if you move forward with an offer) year end financial statement for 2025; terms of each Rental Agreement; who pays which utils (and LL cost); what is the Tenant parking situation; who owns the major appliances; when was it built; is there know asbestos containing material or lead based paint; has plumbing or electrical had any significant upgrades; has main sewer line been scoped within the last year; have there been any leaks, anywhere in the building in the past 5 years; size (btu) and type of water heater(s); size and type of AC unit(s); is there a common laundry area or individual hookups in each unit; is there a wired fire alarm system; is there a fire sprinkler system; is there a security camera system; how old is the roof; how old is the exterior paint (siding and/or trim); who performs groundskeeping and at what current annual cost; how is regular and large or bulky item trash removal handled, and at who's cost; is there any pest control provided, and at what cost;  is there a "system" of keys for the building (type, master keyed or not, controlled access via programmed prox readers), and a few more that escape me at the moment.Be sure you understand the legal boundaries that the Selling Agent is bound to.

I'm not mistaken, then that makes residential investor DSCR thresholds much easier to achieve, no? 

It's an achievable goal.  

We own an operate a fair chunk of larger properties (200 unit+).