@Marcus Auerbach, I see I haven't thought about the competition part of it all yet, but I now see more clearly why it might be easier to invest in a market your close to.
And that's why I want to know how to decide between two markets! (I mean that playfully of course). I know they're both good markets but for different reasons (From what I can gather). I personally am leaning over to investing in Milwaukee for the cash flow available, I'm hoping this'll play into my psyche and motivate me to invest more and better (Hopefully my brain will see the "quick results" and push me further, though I will admit investing is a slow game). But that doesn't mean I'm going to neglect Madison, if a good deal does pop up I'll definitely check it out!
That leads me to another question, if your willing to answer of course, to you professionally what is more important, in whatever standard, appreciation or cash flow? From what I've read cash flow will get you through hard economic times but appreciation might yield better profits. Any response is appreciated!