Happy to talk further on the area (we are large enough to offer options to focus on student rentals/UW Madison campus, and anything from Class C to A locations or suburban/surrounding communities) but to help you consider broad initial search, you could start by deciding how important cash flow is. 

Just don't combine old and class D unless you have a very good reason. 

We're renting that out anyways but sincerely I missed the boat on starting with a multifamily home.

I like to stay in the working class areas as they make enough to pay the rent and bills, but don't have the financial discipline to save enough to purchase their own home. 

We connected with a jet ski and boat rental company near our lake for a discount and commission per booking at one property. 

Quote from @Levi Perl: Have a class C property. 

Class midwest issues. 

The collateral is so so and some have preferences such as certain asset classes they will invest in, but generally speaking, you can obtain an equity deal with very little skin in the game. 

One effective strategy to maximize unit potential is to explore opportunities for adding extra units, especially in C-Class properties.

Or it is a working class area with a lot of jobs that are likely to be heavily impacted by a recession.To understand these risks, unfortunately, takes experience.