But for an OOS investor one consideration is access to support, first of all PM & contractors, and you have more choices in the much larger Milwaukee metro area than in a smaller submarket.

You’ve made a great choice diving into real estate investing—it can truly be life-changing.

If you know what you do and why you're doing it, there's no need for the bad and the ugly, which I personally haven't experienced.

Honestly, over leveraging is a really bad idea at this time (just my 2 cents). 

I can buy investment RE but due to crazy bad DTI (far worse than 100 to 1, possibly approaching 500 to 1), I cannot get reasonable financing on an OO and not sure my co-sign will help on conventional financing.  

Better an empty property than a bad tenant. 

Leveraging business credit for a real estate deal, especially if that credit is only interest-free for a short window, isn’t automatically a bad idea…but it’s definitely not for everyone.

I think you are letting your feelings get in the way of making bad business decisions.

A bad cleaner that is not paid well would tank your revenue so I think it's a blessing to have a well-paid and amazing cleaning team. 

All the markets you mentioned are solid choices for affordability and long-term growth potential.If you’re looking to narrow it down, consider Indianapolis or Columbia, SC, as both have strong rental demand, landlord-friendly laws, and stable economies.