And if their both right or wrong-how to handle this situation?

Some situations where they (the projects) do not go the way of making the profit as you wanted, but there are still deals out there to be had.. 

You have provided a variety of situations where doing a cost segregation study would be useful.  

In this situation, is it better to get a property through regular means, look what is on the market (through realestate agent), or maybe go through a sheriff sale?

In my situation if I’m earning $18,000 in cash flow from a property my tax benefits are offsetting at least that amount and I’m still paying $0 in taxes so the real estate scenario is attractive to me.

I'm sure it was highway robbery - it certainly was based on the man-hours it took - but when you are in a desperate situation, you do what you have to do to get yourself out of it.  

If you are just getting started here in Chicago, house hacking is the ideal situation.

Considering doing a 75% cash out refinance > 30yr 7.45% interest rateIn what situations might the 50% Rule provide a misleading picture of a property's financial health, and when would relying solely on the DSCR potentially overlook important factors? 

Consider defining clear roles, ownership percentages, and responsibilities upfront, and ensure you’re protected if the partnership doesn’t work out.Since you already own properties, it might be worth consulting a CPA who specializes in real estate for advice on tax strategies specific to your situation.

Depending on the situation, a taxpayer could offset some of the passive losses with active income.