If you're applying for a Conventional/FHA/VA/ or USDA loan, then they will do a "global cash flow" where they take into account your PITI (Principal + Interest + Taxes + Insurance (hazard and flood) on all properties (second mortgages included), HOA payments, car payments, student loan payments, credit card payments, and installment loan payments in the numerator and your gross income in the denominator.

This is with emphasis on being able to support oneself during the process.

Not sure how far you are from Chicago proper, but the ULI (Urban Land Institute) is a global group with chapters in most big cities. 

This city hosts a vibrant, diverse community with a strong emphasis on family-friendly activities, educational opportunities, and cultural events that enrich its residents' lives.

But I would plan to reinvest 100% of the cash flow into asset upgrades because our 100-year-old buildings need it.I think there’s too much emphasis on residential and even multi family.  

This quote below is from your link with bolded emphasis by me:So, even if you materially participate in running your rental properties, you still can’t deduct those losses against other nonpassive income.

This includes global behemoths like Blackstone and Apollo.

Thanks,Miguel Suarez I heard a stat that Arkansas will be unlivable in 50 years due to global warming.

However, I feel like there's a lot of potential to run into a lot of walls/pitfalls that can cost a ton of time/money if I do this route.At the end of the day, I want to put a lot of emphasis on using the newest technologies to streamline the business as much as possible. 

A common metric they'll look at is your Global Cash Flow/DSCR which will be affected by your cash out refinance (higher mortgage payment than you've had in the past. 7.