Hi @Reed Meyer, it is awesome that you are getting into real estate investing right out of college. I started investing at 25 in a condo in the NW suburbs that I got pretty lucky on and recently bought a condo in Irving Park that will allow me to live below my means and then rent it out at a decent investment.
I know there are people on here who are more knowledgable than me but I will give you some insight into what frustrated me the most. My dad is in construction and pretty much any 2 flats/2flat+in law unit/3 flats were either in tear down shape, needed 100k to fix them up, or had been fixed up with new appliances but the bones were abysmal and not worth my risk appetite.
My opinion on what you should do: Buy a 3 bedroom condo in an area that you and your friends wouldn't mind living in. Off the beaten path in Logan Square or off the Brown line in Irving Park. You will still need probably more than $20k. I wish I would have done this but didn't consider it until my friends and I were in positions to not be living with 2-3 roommates. Hypothetically, you could put yourself in a great position after 3-4 years if you get to live rent-free and save an extra $15k a year. I have found, sometimes the best investment is finding an opportunity to bring in some cash flow while also living as cheap as possible.
I have worked with a great investment broker who came up with some unique financing options for my investments so let me know if you would like his contact info. I can share his IG account which demonstrates his understanding of financing and investing.