This will help with your comps knowing that they will eventually be used in your appraisal.

As such your underwriting should treat this as a duplex.I suspect eventually virtually all of Chicago will allow additional units but it could quite a few years.  

Now after consulting with a number of RE CPAs I found out that the legal structure you created is the most tax inefficient strategy for california residents and eventually I may be paying a big tax bill year end unless I do a major surgery and spend a lot more money to get it fixed. let me know if we can 1:1 sometime soon to discuss it more

Will these folks prefer to buy suburban or rural homes, or will they want to rent and eventually buy within the city?

Eventually, once the units have appreciated a bit and the mortgage has been paid down to the point we have 20% equity, we split the parcels into individual town homes and then she refinances her unit out and I refinance the three units out or sell them. 

@Michael L.The said company might have to rent the equipment at first but eventually all successful companies will have their own equipment.

Eventually she moves out and on to the next and we manage the property together.

Even if you do I would sell this unit.The negative $3k will decline with time and eventually go positive.  

You know a stove will go out eventually, you know the estimated price, you know the estimated date, you don't know exactly when. 

Additionally, I am willing to live in one of the units for a year.My long-term vision is to buy everyone out and eventually own the property entirely.What are some common deal structures I can explore based on my contributions and end goal?