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.

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.

There are two small beams about 2 inches apart at the top and another two at the bottom. 

I tried to stay out of the way, but I had to stop several things from being done wrong—spaces between kitchen cabinets that were too small by at least an inch for the appliances to fit, a walk-in pantry being built that was too narrow for anyone but a child to get into.

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.

I would warn you though as soon as you give an inch, the next month if rent is not paid on time you may have opened up a door of forgiveness that was not intentional.

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.

I am definitely juggling a lot, laying the foundation to eventual financial freedom is fighting tooth and nail for every inch.