You've found that perfect 3/2 in suburbia, same question.You've found a nice 4-plex and want to start REI, same question.Debt free is a choice, feels great, but usually eliminates many other opportunities (unless your sir name is Rockefeller).

You should now eliminate Property Management and do it your self.  

Now we see that the President wants to eliminate all tax deductions, except for mortgage interest and charitable contributions.

But aside from those, even liens or interests that were acquired or recorded before the tax lien are eliminated. 

After pulling cash out, I like to make about 200-300 month cashflow generally speaking and I have a strong preference for single story typically which eliminates alot of what I see and has put me in a narrow minded predicament probably:)

A downfall is it typically eliminates the ability to have parking forcing tenants in your front building to do street parking.  

if the inlaw unit is known to the city (check DBI records to see if a notice of violation exists), then they won't let you (easily) "eliminate" the unit, and you're stuck legalizing it.

And you can always add cash from any source to minimize or eliminate the need for a mortgage.Of course though we've got to address your use of the dreaded 4 letter word "flip".  

We'd like to know how BP members are going to be affected by the potential of this bill passing?https://www.wsj.com/articles/1031-exchange-a-cherished-real-estate-tax-break-faces-extinction-1497351605 

Although I have a few other ideas of how to possibly make other arrangements work as well.I would hope that the contract would eliminate almost all need for trust, in the sense that should either party not fulfill their side, the other will be adequately compensated.