Simply providing information pertaining to legalities.

Some people see it as a way to get into a multifamily house at a lower downpayment and interest rate, while still providing themselves a place to live.I think the only way it would be "wrong" is if it puts you in a situation you can't afford or makes you "house poor".My husband and I rent out 4 of the bedrooms in our house plus a bonus room, meaning we have 6 roommates, but our entire mortgage is covered.

By securing long-term tenants and maintaining the property’s condition, I’ve enjoyed consistent rental income and significant appreciation in property value.

A 5 plex vs 13 plex can have considerable financing considerations.. a strategic mortgage partner will be critical to answering some upfront questions to provide a property search framework. 

I don't believe they use any security instrument.

Whining about the internet you provide free as a courtesy?

For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?

Any direction you can provide to locate deals, and advice on the area in general would be greatly appreciated.

You need STR insurance, not a homeowners policy.Don't depend on any insurance provided by a listing platform. 

Land Trust" for more information.The trust keeps you anonymous, and the LLC provides a legal barrier in the event the anonymity of the trust is breached and there's action taken against its trustee.