We actually did own several strip centers right after the last crash.

If not we will rent, leverage a DSCR loan, and play the long game like you mentioned.   

Hello, I've had a property in the Graysville area for about 4 years, and the last year has been an absolute nightmare with my current property manager due to it being almost impossible to get in touch with anyone or get responses to emails.

Foreclosures are expensive and take a long time, it would be much more beneficial for the HML to extend. 

For some context, with MLS data, last year in Madison, the median sale price of a 3 bed, 1-2 bath home with under 2,000 sq ft above grade was $394,960 and average almost $419k and similar pricing in Dane County overall as buyers move out to surrounding communities in search of more affordable options.Milwaukee is a big market I am not that familiar with as I live in Madison, WI, but if you decide you have an interest in Rock County, prices can get in your price range in places like Janesville and Beloit, WI, but still mostly above $120k (median sale price last year in Rock Co with that home criteria was $253k, but sales did take place in your price range if you end up in that area of south central WI. 

I need a contractor for a 1915 downtown Hillsboro home I've been eyeing. 

I'll have eyes on it soon 

I had my first investment SFH reappraised last week in a B-class area of KY.

The downside is that the rates are usually higher, they’re often variable, and it’s not long term financing, so you’ll need to refinance later. 

Identify your "why" behind investing in real estate first (cashflow to leverage yourself out of your career, equity build-up long term for retirement, lifestyle investments you can use personally, reducing tax exposure, etc).