But in this city, your financing strategy can make or break your deal.Here’s what investors should know about buying, selling, and financing property in Chicago right now.Why Chicago Remains a Strong Market for Real Estate InvestorsChicago offers a combination you rarely find in other major metros:• Affordable entry points• Strong rental demand• Older properties with consistent value-add potential• Diverse neighborhoods suited for nearly every investment strategy• Appraisal upside in revitalizing areasNeighborhoods like Avondale, Bronzeville, North Center, Uptown, Albany Park, Portage Park, and Rogers Park continue to offer a mix of appreciation + cash flow opportunities.Financing Determines Your Strategy — Here Are the Top Programs Investors Use:1.

If you’re just getting started and don’t have a ton of capital yet, one of the best entry points is the FHA house hack.

Lower entry points and steady tenant demand. 

For example, here in Memphis we’ve seen a lot of success with BRRRR deals because of the lower entry prices and steady rental demand - but the same principles apply anywhere.

.• If you paid LLC #1 with cash-out or equity, record that as “Due to LLC #1” (intercompany payable).Big picture:LLC #1 got reimbursed for all the money it put into the project (purchase + rehab) and keeps any cash-out.LLC #2 now owns the rental and carries the new refinance loan going forward.It’s simply an intercompany transfer wrapped around a refinance.Two sets of books, two clean entries, and the numbers stay honest.

If you’re restructuring a BRRRR deal or repositioning a flip, don’t just chase lower rates — look at how to structure the loan for stronger cash flow or faster execution.In my experience as a private money loan broker, investors who approach 2025 with a readiness mindset (updated docs, clear exit plans, access to alternative funding) are the ones who’ll capture the best deals as the market resets.Curious to hear how others are financing their pivots — are you tightening, holding, or preparing to scale?

So your $300/mo cashflow may look good on paper with a possible ROI of 15+%, but lower rents will likely keep you in the same situation when it comes to expenses. 4) Appreciation is stronger in NJ, and most experienced landlords will tell you THIS + Equity is where the money is made; NOT monthly cashflow. 5) As Shawn as alluded to, there are ways to purchase buildings in NJ for less than 6 figures.

The Midwest is going to strategically matter more in the future and population will be growing due to fresh water and cooler climate, also fewer storms (lower insurance premiums).

They want contemporaneous records—evidence created at the time the work was performed.What real documentation looks like:• Time logs showing date, specific task, and hours (kept weekly, not recreated at tax time)• Receipts for cleaning supplies purchased the same day your log shows cleaning work• Calendar entries blocking time for maintenance with notes on what was done• Text messages or emails showing you personally handled guest issues• Photos documenting before/after repair work with timestampsThe extreme but effective approach?

I don't think there's a chance that bigger builders are going to lower their prices and "create lower comps" to compete against.