2nd liens are the best way to lose your money, are you lending personally, or are you working as a broker? 

@Moira Baggett, there is no real answer to this other than: review your operating agreement and potentially talk to an attorney, likely to do the same.Most syndication docs drafted by capable attorneys will effectively state that you are acknowledging these are risky investments and there is a real chance you lose all your money.  

There are so many stories of people losing everything even with millions in insurance coverage.

Even if you aren't gap funding, you could lose any equity stake with punitive default interest and also risk the HML calling the note due because they disallow 2nds without an intercreditor subordination agreement. - On the subject of gap funding, just don't.

“Bad” if they lose all money, or if they lose some money but fail to communicate.  

Account ClosedI'd house hack locally.  100%.And IF you are serious about OOS BRRRR in the Midwest - you're going to need to spend some time in person in your chosen market.If you buy a random property that you haven't seen just because people you don't know tell you "it's a deal" - you will lose money.

And, how much cash do you want to lose every month?

If I were to create a single-member llc and give my wife 100% control, that seems like I would be at risk of losing everything in case of divorce (god forbid). 

I'd be able to make a couple of hundred a month that way, but I lose a lot of tax benefits.My preference is a lease option, but I'm struggling to price this out.

If a potential guest has questions pre-booking and you take too long, you will lose bookings and revenue.