If you are using STR, REPS, or self rental with material participation to convert to active or nonpassive income, you do not have to do this if you have passive business invesment that produce passive income that will exceed the loss generated by depreciation.

When you converted the 3rd unit and put it on your tax return was it done through the city?

You should track your own units expenses as well so when you move out, you can quickly reclaim any expenses or depreciation you built on the personal unit when converted into a 2nd business unit which would then be included on your schedule E.You also write off half of your property taxes, insurance, HOA dues, or any shared expense.

Building a new ADU will put you in a more “negative equity position” than converting a garage for example, which only cost <200 per sq ft.  

I own a multi-family house that was converted from a single family, therefore, there is only one gas meter.

Then have a 6 month period to convert all old currency $20 and $100 to new currency.  

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

Currently our favorite idea is a SFH we can convert to an up down duplex by sealing off a staircase with an ADU on the property for us to live in.

Some rehab lenders have favorable refinancing programs to convert the rehab loan to permanent 30 year financing.

During this 24-month period, the property must be rented to another person at a fair market rental value.After the 24 month period your sibling could convert it into a primary residence.