I've seen some people house hack a single family home by renting out the rooms, but keep in mind that traditional lenders would not be able to use the income from renting out the rooms (known as boarder income) towards additional income on the application.

The few people I've talked to don't really have good opinions on it. 

And you’re still not in Nazi Germany.BUT, Donald Trump is about to make a lot of people rich.

In my experience, most properties that go to auction end up overpriced so I'd be prepared to attend a LOT in order to get something that worked on paper.When I attended my first market auction with an experienced agent the advice he gave me was to figure out my maximum beforehand and stick to it (Seems obvious but people get caught up in winning).

Most people looking to hire on there are looking for cheap bookkeeping.

Every tax season, I see people unintentionally overpaying the IRS.

In Oak Park, we have had people like Ray Kroc, Ernest Hemingway, Bob Newhart, Sam Gianncana, Betty White. 

But wanted to ask here what other people have done or if you have any ideas.

I am looking for advice from people who have done this in the past.

I appreciate you listing the steps you took / people you went to in order to fill the gaps.