@Joe Michaels, What a lot of investors will do is to use the 1031 exchange as @Michael Plaks said, isto actually "acquire" additional depreciable basis. 

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

The filing fees with the SEC are usually minimal, as you’ve found.

But this comes with pockets of C/D neighborhoods, and higher potential for headaches;  in addition, appreciation in these zips has probably maxed out for a while.

I’m not focused on volume, but rather on maximizing the assignment fee per deal, compared to doing multiple smaller deals to achieve the same result.My question is: Where can I find sellers with messy titles?

Ok it might not be 1:1 but it will add additional revenue.

The law does NOT apply to landlords:With less then 5 rental unitsThat live in one unit of a duplex and rent out the other unitThat rent out rooms in the home they occupySo, landlords can no longer state in their rental ads, "Section 8 not accepted".The reverse is also true, "Section 8 only", cannot be used.We've always recommended screening S8 tenants the same way as cash-paying tenants.Landlords waiving application fees and/or security deposits only for S8 prospects may also be violating Fair Housing.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Would it be legal to wholesale a family members home (est. 1M), and receive a fee for the wholesale services? 

These folks wont tell you not to pay them massive fees!