I would reexamine your transactions as there is probably more expenses available to you that can reduce your taxes.

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

This is a home that my family wants to live in, so we are okay with the repairs being more expensive then what would make sense for a property that is purely an investment property.

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. 

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" 

What's your monthly expenses and resulting cash flow? 

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.

In a softer rental market like we seem to be in now, it becomes much more important to focus on the boring fundamentals like controlling expenses.