We manage our own, but there's not a lot of great choices of PMs in the area (which is why I decided to manage myself). 

There are a bunch of good choices IMHO.We don't have leather but all our surfaces are super durable because they are higher end sofas and chairs.The 3 main couches are a pair of Basset and a La-Z-Boy.

I will go so far to say that the sub-metering was the WRONG choice for us, given the cost, and given that if push came to shove, it would not hold up under scrutiny - by tenants, in a court of law - and therefore by extension, us.

The choice depends on their priorities simplicity now or long-term tax advantages.

A duplex or triplex is a solid choice for house hacking, and this community has tons of resources to help you learn how to find and analyze deals.

If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

I have a little bit of a choice personal problem.

Hi, it is your choice.

Either choice you make will be a good one.

Option 1 seems like the safest and most flexible route.