So I'm trying to weigh selling my rental vs keeping and renting out through a management company. 

A few investors I've worked with have gone for projects that are huge to start with because the project looks extremely profitable and then suddenly they are overrunning the project costs.

Someone didn't hang up the phone and actually IS interested in selling (the first time this has happened so far). the only thing is the home is a mobile home located in a senior community.

I house-hacked a duplex back in 2018, and now I'm debating if it makes sense to sell.

I was concerned that the houses don't meet the 1% rule but with older houses, you're losing in more repair costs. 

I'd say all the stats are similar from Cincy, Columbus, and Cleveland EXCEPT we are a lower cost of entry by $36k(cincy)-63K(columbus)!

This change is significant for the financial feasibility of ADU construction in Chicago since water service costs can be more easily justified when collecting rents from two additional unit.Also proposes to allow larger units and to allow ADU construction in any zoning designation.

To save money on closing costs and interest.

If you had the funds available, with some cushion, is it advisable to skip the HML and $7-12k cost, and purchase in cash?

If done correctly this is a great way to replace damaged item without a cost to the host.