The management company I use for my long term rentals has several employees that get their degree from Stout in Property Management and routinely hire part time help that are working towards that degree.  

Routine maintenance went by the wayside, the original owner passed away and with him the foundational knowledge necessary to keep the place going, but the kids struggled on with the property.

We are and have always been strictly cash buyers.

What you can do is learn all you can starting now about personal finance and how to manage your income and debts, what debts are good and what debts are bad, payment routines, etcetera.   

You can see the chart below (one of my faves ;) to get an overall idea, based on a long history. bottom line is that many millions of dollars were made in the Bay Area strictly due to appreciation.

Someone said monthly rents total $4275 but that is strictly blue sky (pro forma LOL) as no one has rented there recently... the location is prima and the yard has been well designed.

I routinely hear people talking of creative financing with lenders.

After you're more established and can show them at least 2 years of income statements, they'll have something to work with and your probability of getting them to lend to you will increase.Another strong variable is if you intend on purchasing the property strictly as an investment, or if you're going to live in it as a primary residence as well.I am in no way a professional however, and I would still suggest you contact a loan officer and see what kind of insight they have for you.

Make sure to verify during your final walkthrough.Talk to your attorney about the specific requirements in the handling of security deposits, as Chicago has very strict laws regarding security deposits.

Should I underwrite this as a strict 4 unit, and call the 5th the icing on the cake?