The interior was outdated, the landscaping was overgrown, and several deferred maintenance issues were apparent.

You are micro-analyzing the minutia of each offering, but that's not really the issue.

Purchasing a STR in a somewhat sketch area is a terrible idea and as others have mentioned, is going to open you up to potential issues. 

The foundation was already approved, permitted and finaled years ago for a 3400 sf house, and its solid and I won't be building directly on the overhang edge; but rather back away from the edge a few feet to prevent any load issues all the weight will be on the longer sides of the existing footing.

I've been teetering around the idea of house hacking once I am done with college, but a big issue I have come across when speaking to a mortgage broker is the fact that I need to prove 2x of the mortgage in monthly income.

Usually an issue if older door is salvaged and new locks are installed that don't quite match up with the old door strike plate location.

That's the reason why we sign leases in person, so we can go over the main issues in person and make sure they are understood. 

If you can identify property you can look up property on county website.If you know the owners name, Google can do wonders to get contact info.Why do you think property is underperformed?

The kitchen became an issue towards the end.

There is no issue with eviction for non-payment of rent during the winter in Wisconsin.