Obviously lots of research involving zoning, codes, and the rules in the area, but it can be done, and these types of properties usually cash flow well since they aren’t advertised as multiple units.

You do not need a full (2) years that for banks/lenders who have strict guide lines or "Overlays".

Egressed a basement window to code, expanded master bedroom, built island, added dishwasher, added new washer/dryer set, sewer repair, new electrical box.

Strictly speaking on the letter, ask yourself if you were the lender “Would I loan money to this person?” 

@Alex GrullonGreetings from ATL/North Georgia.Target mom and pop multis in areas where the eviction moratorium is being enforced strictly.

Not sure what code has on that. 

Before you do any of these or put effort into them you should consider zoning law and code.

I have seen some advisors structure the transaction where the four individuals enter into an agreement whereby they are holding legal title to the replacement property for and on behalf of the four member LLC as its agent strictly for credit/financing purposes, but you would need to be very careful here. 

If so, most codes require them to be replaced. 

My understanding has always been that if they stay after the expiration of their Lease,  that is enough to trigger the MM Lease in Chicago.Where is that code section?