Considering buying the corp so avoid land transfer tax - that might help with the numbers.

(Loan paydown, tax savings, etc etc..).

And, if you are going to buy someone's time and expertise to train you, DO THE WORK. 

Did you inherit this home with a step up in tax basis or will you need to pay taxes on any gains if you sell?

Even using dedicated independent contractors as your maintenance crew requires book keeping (bills receivable, payment, bookkeeping to track expenses for tax purposes and warranty claims, etc.).Having a reserve for cap ex, but not allocating any estimate for the cap ex cost means that your cash flow estimate does not include cap ex. 

A lot of Chicago workers are moving to this area to escape IL taxes and politics.

Also, you will have additional occupancy tax depending whether you are in the city limits or not.

you'll probably still need something long term like software as others have suggested but this was a thought i had... you could see the actual profit or loss from a tax perspective for each property.

His expertise in IRAs, trusts, and asset protection was truly impressive.

A successful rental property should offer positive cash flow, meaning your rental income should exceed your monthly expenses (mortgage, taxes, insurance, maintenance, etc.).To find the right tenants, ensure the property is priced competitively within the local rental market.