The short answer to Kaleb is that 'yes', people in BP Nation have 'experience developing or owning something like this.'

I’m loyal with people who provide good service.

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. 

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).

Cut your losses the first time they miss a payment and start the eviction process.

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

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

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

One other thing that people in their 60s can consider is - if you are planning on taking Social Security and making passive income part of what you live on, rental income may not count as income against your Social Security benefits.