Hey Naeem,
I know I'm in the minority here, but I don't believe you should shy away from these neighborhoods at all. The cash flow in the areas you describe can be immense and there are many ways to mitigate the risk. For one, tenant screening will be very important to you. Take the time to make sure you are renting to qualified responsible tenants. There are definitely plenty out there. Secondly if you want to rid yourself of some of the hassle a trick I heard from a friend who was house hacking, is to not let the other tenant know you're the owner, You're just another tenant who the owner hires to fix things every now and then. Set up a payment system with a degree of separation and communicate through email. That will give you a little less hassle when you bump into them on the way to work in the morning.
P.S you should skip the 2/3 flats and go straight to a fourplex. They still qualify for all SFH benefits and for a little more work you have 25% more ROI. Also the more doors you have the less any one thing going wrong affects your bottom line.
I'm bias, as I'm from the west side of Chicago myself.