Im just outside of chicago and in the suburbs and condos are not that expensive and i could make ok cashfflow from one.

This generally means that the rehabilitation costs must exceed a certain percentage (often 100%) of the building's adjusted basis.Qualified Rehabilitation Expenditures: These are the expenses directly associated with the rehabilitation of the building.

For your five rentals, you can have a separate "personal" checking  account (or several) that will be separate from your personal checking you use for your own living expenses. 

The issues are the nontransparency and expense of doing that. 

I am the remainderman on a Florida "Ladybird Deed" (Enhanced Life Estate) on my parents home.

In the multis I have now I do enhancements after each tenant leaves to push the value because one day I will sell. 

Don't we all wish that all rental properties would cover the expenses no matter what.There are TONS of variables to factor in (price point, area, market, condition, etc), but at least in my market (Indianapolis) the rents on a SFR often do not cover all expenses.

If you had a side hustle lets say with an LLC (has its own bank account, expenses, income, etc) You could most defiantly write it off under "education expenses" 

[ but this will be expensive] .

I moved to Columbus a few years ago (from Portland, Oregon which was super expensive) to become a full time real estate investor, and ever since, I've completed quite a lot of BRRRRs, flips, and own a successful rental portfolio here in Columbus Ohio.