Clark,Excellent question, and thank you for asking it directly.My reasoning is simple: at this stage, single-family and small multifamily deals are well within my current execution capacity; I can source, underwrite, renovate, and manage them with a high degree of control and minimal outside dependency.Larger apartment complexes, however, require a different level of capital, operational sophistication, and speed of execution that far exceeds what I can reliably deliver alone today.

For a renovated Pilsen 3-flat, somewhere $10–13K.Also check rent comps for new construction Woodlawn: if more buildings deliver, you may be competing through concessions or slower lease-ups.If it were me and I wanted a smoother first few years, I’d choose Pilsen unless the Woodlawn building is truly special or priced with enough cushion.Happy to run the numbers with you if you want to stress-test both deals, Chicago is all about underwriting the next tax bill, not the current one.

@Ramsey Doumani Ramsey, we've delivered over 600 investment properties and none are condos.

If an owner or operator is willing to vouch for a PM, that’s a sign they’ve delivered real results.4.

Fewer still actually show-up to deliver the value in-person. 

Domi gives your home address a unique digital ID so all your physical mail, including bills, statements, government notices, and even junk mail, can be delivered digitally.

Similarly, adding units doesn't automatically make an investment safer; it simply multiplies the points of failure.Bottom line: multi‑family doesn’t automatically equal more reliable income—in fact, it often does the opposite.For over 17 years, we've delivered more than 600 investment properties using this process: start by defining your financial goal.

Because they see transactions every day, they can usually point you toward the wholesalers who consistently deliver workable numbers and away from the ones who over inflate ARVs or hide important details.Here are a few things that work well in competitive markets like Staten Island.How to locate active wholesalersStart by showing up in the same spaces they operate in.

As @Adam Bartomeo mentioned, one of the units has to be delivered vacant and you need to be able to occupy the property within 60 days.

Do you have a long history with your contractor doing 200k-level rehabs, and has that contractor always delivered on-time?