The neighborhood is mixed single family and multi family, with this property located on a more multi-family dominated street.I have good job security, $88k base pay with an additional $15k in bonuses last year.

FHA is going to be a more expensive option, but still very viable. 

@Nathan Belete Although I am new to real estate, I have lived in Milwaukee for many years and want to expand on what @Brett Kash said in a more general sense.

If he wants all his cash at once you could buy the house from him using an FHA loan once you qualify for the loan.It sounds like if this one does not work out you will be in a position come September to qualify for a loan yourself and not have to go a more difficult route.

I moved from the west coast myself to get into real estate in a more affordable market - its been 5 years and I haven't looked back.

A lot of people do mock signings with a more experienced signing agent before they do their first.

You could probably triple the amount of units you have by going out of state to a more landlord friendly area.

On a more serious note, I think there are a lot more like us (older, with jobs and families, slugging it out) than there are wunderkinds making it look easy.

When I finish renovating that 3rd home  i will refinance and cash out equity and repeat process on my fourth with a more conventional loan and True BRRRR strategy.  

These are maintenance costs and cap ex is usually bigger item that you expect to repair, replace on a more routine basis.