William, there are pros and cons to every market. Some areas make it easier to succeed than others but I don't believe there is a perfect place to invest. There are drawbacks to every geographic area, investment strategy, etc. I like the idea of getting started locally when possible. Looking at your pros and cons: there are plenty of deals that cashflow in Milwaukee. Houses are older the closer you are to the City and they get newer the further removed from downtown you are. I don't believe finding a PM, team, etc. in Milwaukee is any more difficult than any other city. If you need help or contacts; I'm happy to help where I can.
You also said in a later post that you are looking to stay in Milwaukee long term because you don't have the career options for your line of work in KC. IF you invest in Milwaukee and are concerned about the crime you need to look into that further. Just because the crime statistics are awful in Milwaukee, that doesn't mean every neighborhood or suburb is a high crime area. I believe there are some crime maps online which can help you decide which neighborhoods work for you.
-Troy