Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc. 

I am not a tax expert, but here are my thoughts. 

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

I owe my lender about 8k. 

I'm a realtor from Colorado who wholesales STRs nationwide to help investors get big tax deductions.

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

If you are not familiar with Scott, Scott was the Executive Director of the Opportunity and Revitalization Council, which was tasked in part to support and advance Opportunity Zone tax credits during the first Trump Administration.

I shifted from investing with a cash flow focus to the appreciation and tax benefits side of things.

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

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