Hi William,
I am fairly new to the Milwaukee area and I too just started investing in RE here. Any advice I can provide is strictly from my little experience and the education I’ve gotten in the last two years.
Like you, I wasn’t sure where to even start, so I figured I’d just immerse myself in this whole RE investing and stop being afraid of failing. So I purchased a Duplex in Milwaukee. The top unit was already rented, the bottom unit was vacant and is in the last stages of the renovation. I am not handy and I know I don’t want to deal with tenants, so I hired a property management company that charges me a flat fee of $95 to manage both units. They take care of everything, collecting rent, screening tenants, getting the property ready for new tenants, evictions, maintenance calls, utility bill payment (Water), repairs, and will even make your mortgage payment for you if you request it etc. At the end of the month they send me statements that show the activity for the month and all I do is make sure that I have a deposit in my account a few days later. I want to be as hands off as possible, because one day I want to move to a different state and I might want to keep my rental properties here. Any repairs that need to be made over $300 need to be approved by me first and I decide if I have them take care of them at their rates or I can have my own handyman/contractor take care of them. Once the bottom unit is rented, in the next few weeks, I have calculated cash flow from that property to be about $500. Like I said, I am still learning, but if you have any questions I’d be happy to help.
Best of luck to you!