This raised the question to the other tenant, "would I be docked for late rent on my credit score if the other tenant doesn't pay on time?". 

Rents will keep raising in most markets so bank on that for additional cash flow in the upcoming years.

If things start getting tight, you can always switch to doing work for clients too in order to raise funds. 

Wasn't aware of the whole copy paste situation.

What legal requirements should I be aware of?

There is a big distinction on the variety of restrictions you need to be aware of with ADUs in Chicago specifically.

I could go on for hours of the horror stories, (squirrels raised by tenant's) yeah!!!! 

I would say from my experience flipping myself and seeing through my clients' projects that the main things in this market you need to be aware of is that houses are taking time to sell, they're selling for less than expected, and they need to be quality.

Some lenders would raise the 20% with private investors through PPMs or unsecrued notes bank does not allow junior loans.

We put a sign on every property to: attract tenants, create brand awareness, and to help prevent scammers from using our properties as bait.