As far as a multi, personally if all things were equal I'd go for the multi for a few reasons.  1) Added diversification.. if one tenant doesn't pay, you can still cover property expenses with the other tenants 2) Shared capex... typically, one roof and one property to maintain but multiple streams of income 3) Less vacancy.. usually multi's rent for lower, for example one of mine is the sweet spot of 3 bedrooms for $1300. 

Target Distressed Homeowners -  there are over 600+ pre-foreclosures in Miami 2.

With commercial DSCR loans that have prepayment penalties, (could be similar with other products as well) if you make a principal payment before the pre payment penalty expires, it will trigger the fee.

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

.- maintenance/cap ex at $192 is not enough to cover one unit. 

We were reached out to by a migrant housing group member asking if we would house a immigrant member/family/etc. where the nonprofit would provide a 12 month stipend to cover for the "whole" lease.

I give pre-access drug screens to travelling contractors that come here to work short term jobs in a refinery. 

I can't imagine any renter leaves it clean enough to move in a renter right behind without decent cleaning it unless you had a diligent renter that paid for a cleaning.You could add a clause in your lease stating a charge for cleaning upon move out if you insist that the renter cover the expense.

Is there an existing Chicago real estate discord group I could join?

Buy Box / About Me: 1) Class B+ or A area 2) long term buy and hold 3) Seeking cash flow and appreciation (fine breaking even with rent if long term growth exists) 4) Good school system and economic growth in area 5) seeking area with young family and rental demand