I don’t know anything first hand about the market, but I looked it up on Airdna.  

I’m thinking a small town could be a great place for me to start compared to big cities.

Adjustable-Rate MortgagesAdjustable-rate mortgages (ARMs) typically start with a lower mortgage rate than a traditional 30-year fixed mortgage.

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

Then once I find a property that I like to buy I'll start looking at the comps in the area that have been rented and are currently on the market to be rented and make sure that my mortgage payment will at least break even with the rental comps.I'm using rough estimates on Zillow and websites alike.

We quit real estate investing and it took me 23 years to start again.

With that said, it's best to START it like you're going to outsource everything, so it will be easier once you decide to make that transition.

I think everyone's situation is different, and when one crafts their buy box, they need to consider their current family and finances.For me, when I started, I wanted to buy 2-4 unit distressed properties in neighborhoods I wanted to live. 

@Mike Levene cost to build per square foot is $200-$300 depending on finishes.So, you can start with that.

It’s been a learning experience, and I think this is the push I needed to start looking at properties that the value comes from the NOI.