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

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.

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

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. 

What's your monthly expenses and resulting cash flow? 

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.

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.