Milwaukee area investors?

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Greetings - I am new to this forum, but not entirely new to real estate. I have successfully renovated & flipped two houses in recent years. However, after much deliberation I have decided to pursue all of my focus on rental properties. Long story short I have been studying for about a year but need to start transitioning into reality and action to get the the promised land of passive income real estate nirvana. 

Anyone with perspective on the relative cash on cash distribution for areas in and around Milwaukee? I see in areas like Bayview and Riverwest the duplex prices are a bit higher but receive much higher rents as compared to an area like south milwaukee or west allis. I am remiss to focus on heavily distressed rehabs which require a large money investment and rely on promise of equity to be profitable. 

I would like to focus on duplexes/triplexes/quads. My short term goal (5 year) is to hit a freedom number and exceed $2500 in cash profit monthly so I can eliminate my reliance on my practice and transition full time to real estate. Current resources include ~$20k in cash, ~$100k in mortgage equity, and ~80k in past employer 401k dollars that I could theoretically convert to a pre-tax SD-IRA with checkbook control if need be. My household income allows me to save $20k post tax dollars a year and ~40k pretax dollars per year for allocation to real estate rather than stocks/bonds & speculative instruments.

Any thoughts on an optimized strategy? As we seem to be ~peak cycle I am reluctant to go all in on an expensive property (quad >$250k) and get hit with a potential equity dip which could impact my short term ability to borrow against and add more properties. However, I don't want to sit and analyze forever and a deal with minimal $ hit even in the event of a shorter term housing correction would seem reasonable. 

Also - what local banks are friendly to this kind of work? Curious what the general process for buying and adding rentals is and how to leverage "other people's money" so to speak, as I feel buying and holding rentals is probably my terminal strategy with a longer term goal of adding apartment buildings to the mix.