@Reed Meyer glad to hear you’re getting started on your real estate journey here in Chicago.
Let me give you some perspective from a “homer”. I’ve lived here all my life, give or take 5 years for pharmacy school and the like, so I feel that I have a exceptional understanding of the areas in the city. Now that I’ve steadily built my cash reserves, I’m looking to execute the house hacking strategy as well. To that end, DONT deplete those reserves.
Secondly, you have to focus on your strategy right? Are you going for cash flow or betting on appreciation? Seems like you want to do the former and I am on the same boat. I have been in negotiations for this 400k+ property in the Irving park neighborhood. I went through the inspection only to find out there would be > 30k in rehab. At those numbers it wouldn’t cash flow ..not even close if I save appropriately for vacancy, repairs and cap ex. So I’ve drawn a line in the sand and will touch base with the property in a couple weeks to months and see how motivated the seller is post-COVID peak. You may not have this luxury given your timeline but I also wouldn’t rush it.
I grew up under the philosophy that the north side of town appreciates faster than the south and west side of town, which tend to house your lower B and C class properties. Unfortunately, this is where you’ll find the sub-300/400k properties but can also run the chance of riskier tenants. I’ve decided that this isn’t the strategy I want to build my portfolio on.
For safe starters, I’d start south in the McKinely Park Bridgeport area(by Sox park and on the proverbial “come up”), then back up north west along the 90(if possible) through the humboldt park area (historically rich in Puerto Rican culture but on the path to gentrification) up to Jefferson Park. PM if you want to exchange ideas or for insight on the city (as I can best provide). Looking to network with like minded individuals in the area.
In the meantime, stay safe !