Interesting situation (Buyer conflicted)

[Blake Clifton]

So I am interested in picking the brains of my fellow BP peeps. Here goes nothing... I was recently approved for a 300k VA loan with no funding fee needed because of my COE. The bank will actually let me go to 424K but I am restricted in one other area that I care not to share openly but would over a DM conversation. I live in the Chicago area and want to get into multifamily. 2-4 flat ideally. I've always been told to never take on debt that doesn't pay you (Huge Grant Cardone fan). I would be terminating my current lease but I am trying to lower my outflow of rent against the difference of getting the multifamily. I've ran numbers against my current lease, exp, etc. I'd reduce my outflow from 2k to hopefully $500-$700 out of pocket a month so a net savings of $1,300-$1,500 as long as 2/3 or 1/2 of the new unit it rented. But I take public transportation to my current job but within the next two months will require me to have use of a vehicle. So there will be a cost of doing business in that regard as well. Do I wait for a deal that will get to me zero out of pocket for the rent?

Chicago is a tough area for that amount (300K) Thoughts?