Some criteria to consider when evaluating a market are:- school districts-crime rate- job/population growth  If the crime is low, schools are reputable, and job/population growth are steady/high, chances are you are looking in the right markets. 

Great job!

The desperation for odd jobs and snarky price increases are going to butt heads.  

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with zero or negative relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560, little to no good tradelines, lots of collections & chargeoffs, recent evictions.

I would suggest talking to other people flipping properties in the area and ask them for recommendations on investor friendly contractors. 

I recently lost my job, have about $150k in cash to invest, have a few cash flowing rental properties, and really want to use the $150 to maximize cash flow so I can avoid a regular job and focus on real estate and starting a new business. 

Look at the job market, schools, and amenities.

I'd highly suggest getting involved in local real estate meetups.

You must occupy for 12 months but unforeseen circumstances such as job transfers and such can reduce the period

Milwaukee got hit hard in the 70s and 80s when manufacturing jobs moved overseas, it took 50 years to recover and that has been going so quietly in the backgound that nobody took notice.