The mortgage has gotten out of hand due to property tax increases, miscalculated escrow, and an increase in my interest rate from an initial buy down, increasing from $2600/mo to $3200/mo.

Ask yourself, why would the federal government pay MORE than market rent and waste our tax dollars?

You should look into whether you can hire an officer to walk through your problem unit and have his professional opinion on whether they are smoking in the unit or if it is a residual smell.

Are those the professional photos? 

Don't forget about your property taxes going up to account for that ADU.

Completely agree with the original post but an LLC is NOT a tax vehicle.

Do that every 2+ years, sell tax free, repeat, and you can be set for life ("live in flips"). 

The challenges are Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

According to the City of Chicago tax code, it costs $5.25 per $500 of the transfer price.