A few quick, practical things that actually matter on multi‑units:For your budget and area (400K, northwest side + Melrose Park), focus on 2–3 units with:Strong bones (roof, foundation, mechanicals)Room for rent growth (below‑market rents, dated cosmetics)Clear separation between units (separate entrances, utilities, meters)An owner‑occupy option so you can live in‑unit and keep borrowing costs lowWhat to watch out for:Parking issues or “we’ll just put a car on the street” arrangementsShared HVAC, shared utilities, or “their own meter but… it’s all run to the same spot” nonsenseOverpriced buildings that only work if you aggressively rent up and rehab cheap—force that math to hold conservativelyFor specific “properties worth looking at,” I’d branch your search into:Chicago northwest side: 2–3 units with long‑time tenants under‑rentedMelrose Park / Cicero / Forest Park: 2–4 units within blocks of transit where you can raise rents a bit but still cash flow at 400KIf you want, I can send you a super‑short checklist for when you walk each 2–3 unit (what to inspect, what to ask the agent, what to run through in your head before you decide to offer).

Spec homes are not super profitable here unless you have a dialed in system...or are like me and dont mind doing work yourself

Private money you are going to be looking at super high interest rates.

@Tylere Weaver this is a super important question and it doesn't just apply to lenders.

John's, Brooklyn College, LIU Brooklyn, and others- Long Island: Hofstra, LIU, Adelphi, Molloy, Old Westbury...Proximity to NYC is very convenient from these areas, but the markets are super competitive, and prices continue to climb. 

Any advice, insight, or lessons learned would be super helpful.Thanks in advance, looking forward to learning from this group!

This is super common with mid-term rentals tbh.

Building permits for rehabs are not super expensive.

Without the converted garage it would be a $255k-$265k house, but with the added sqft, even though not super-functional, maybe $265-$275k.

As a matter of fact if you are a licensed agent, I've seen investors LOSE access because the agent with the deal knows they aren't getting the buy side or the listing, so they are going to present it to someone else first (super unethical in my opinion unless already discussed with the seller, but it is what it is).