All licensing does is provide a consumer who has been ripped off or taken advantage to have some means of regress against a crook.

First time posting and getting into the investment scene, I currently have a single family home that was my previous primary, and looking into purchasing my 1st true investment property, trying to find some advice on the financial aspect of the purchase, here's my scenario;Currently going through pre-approval with the builder and I do have liquid assets enough to cover the downpayment for the property (40k) but I do have a car note (41k, 800 monthly, extra 500 to principal monthly) and a Patio upgrade (25k no interest till March 2025).

It will take a long time to recoup the cost on a property this size. 

I've heard many times that moving NW from Logan Square into Avondale and Portage Park is a pretty foolproof approach.

It really boils down to time.

Send the tenant a written notice that if they do not sign the renewal, then the lease will convert to a month-to-month basis, what the rent rate will be, how they can give notice when it's time to terminate, etc.It sounds as if these tenants are pushing you around and dictating the terms.

You either spend the time categorizing your revenue and expenditures as you go (easier) or at the end of the year (harder IMO).

Let’s say hypothetically the P/I is $8000, the property tax is $30,000 (divided into 4 payments), and insurance is $4000 (one time a year), and the expected random maintenance  is $2000 annually? 

Let him do it, if its not satisfactory at the time of the move out and as long as you have a detailed move in inspection, you can charge him for whatever needs to be done to the yard.

At the time I did it, there was potential incentives of up to $750/unit for the 2 year and $1000/unit for the 20 year.