I moved here from Portland in 2020 to start investing and now own 10+ rentals, and I’ve seen that the macroeconomics are really strong—population growth, job growth, and major companies like Intel, Amazon, Google, Facebook, Honda, and Microsoft expanding here.

I moved here from Portland in 2020 and now have 10+ rentals, and the reason is simple: population and job growth are strong, major companies like Intel, Amazon, Google, Honda, and Facebook are expanding here, and you can still find properties in the $120–180K range that hit the 1% rule and cash flow from day one.

I highly suspect over leverage accounts for a majority of RE investor failures.  

Property Condition & Amenities: it’s important to, “Maintain to the Neighborhood.”Key metrics for each Property Class:Class A Properties:Tenant Pool: Majority of FICO scores 680+, no convictions/evictions in last 7 years.Tenant Default: 0-5% probability of eviction or early lease termination.Section 8: Class A rents are too high and won’t be approved.Vacancies: 5-10%, depending on market conditions.Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Class B Properties:Tenant Pool: Majority of FICO scores 620-680, some blemishes, no convictions/evictions in last 5 years.Tenant Default: 5-10% probability of eviction or early lease termination.Vacancies: 10-15%, depending on market conditions.Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, balanced amounts of relative rent & value appreciation.Section 8: Class B rents are usually too high for the Section 8 program.Class C Properties:Tenant Pool: Majority of FICO scores 560-620, many blemishes, but should have no convictions/evictions in last 3 years.

The majority of quality lenders are all going to have terms that are in the same ballpark.

I am an Executive in a life sciences company which takes the majority of my time and I have no intention of stopping that, but want to build a larger rental portfolio to have other financial / lifestyle options in 10 years. 

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.

We use Section 8 to stabilize cash flow against rising variable costs.With voucher income covering the majority of rent, our repair spikes don’t hurt as much because baseline cash flow is predictable.6.

There are some areas in South City and the surrounding areas that I would recommend to live in that make great options to do LTR's, STR's, and MTR's given their proximity to major attractions, highways, and employers.

I have a meeting with a bank later this week to see if I can get a line of credit for the holding LLC but they require the business to be at least 2 years old under the same majority ownership during the last two years.