Hey Reed, great to hear you're getting involved in house hacking at a young age. I followed the exact same path however with 1 roommate in a 2 bedroom condo in Lake view and am about 1.5 years into it. One thought overall is to start smaller. It can be exciting to want to go all in on a larger building, but there's A LOT about home maintenance I'm glad I learned at a small scale, especially as soon as I moved in there were plumbing issues, dishwasher issue, the blower motor in the units went out as well amounting to about $1,200 in costs in the first 6 months. None of this came up in the home inspection.
I'm now moving out and will be receiving about $500 a month in positive cash flow. I'm planning on getting another property and working my way up to a 3 flat.
Do not and seriously do not exhaust all of your reserves. You never know what will happen, even now there's Coronavirus causing some people to not be able to pay rent. I also had an issue where another unit's shower was leaking 2 floors down into my unit's ceiling. It ruined the drywall and the other unit owner paid for it, however if this was in your flat then it's on you guys to pay for the repairs.
If you still want to go the larger building path, my agent said it's tough to househack and not pay anything especially in the areas you've mentioned. You'll hear a lot of people going to the west side like Pilsen area, although that may be more expensive now.
Please personal message me if you want to chat sometime about all this, I'm a huge supporter of starting early!
