If they are basically heading toward bankrupt then they have a better chance. 

What if one goes bankrupt?

A job that gives you close access to divorce or bankrupt attorneys would also be beneficial in finding deals. 

If a lawsuit is filed the insurance steps in or the company which owns nothing is bankrupted and you are out the start up costs only.Your business entity should lease from each land trust with a right to sublet.A series or bucket LLC in Illinois will end up serving a plaintiff attorney with a hunting license.

It can make you rich, but it can bankrupt you even faster.

On top of that, the condo association (very small, 6 units only) is a disaster and is nearly bankrupt, the shared space (i.e. yard, parking lot) are in terrible shape, and the current association officers won't take steps to collect against past due association fee owners. 

I mean if we are going to go bankrupt let’s do it UP right!

Time to study Economics and pay very close attention to it.To emphasis this point, think of a scenario where if you didn't follow the economics, things would have turned out VERY bad.Take Investing in Detroit before it went bankrupt.10 to 20 years before Detroit went Bankrupt, there were very clear economic signs that domestic autos were in trouble.

It feels like stealing...https://www.zerohedge.com/news/2018-07-31/bankrupt-philadelphia-plunders-its-property-owners-cash

Even though holding a property as a rental will appreciate over time, you still have the asset in the long run.If the owner that you're lending the house to goes bankrupt or something happens, you still have your asset that has appreciated over time where you can repeat the process on a higher ARV home once fixed up a bit, basically