This sounds like a thoughtful plan, but there are a few things to keep in mind.First, while you won’t be on the mortgage, you'll still be co-owner, meaning if things go south (like he defaults), the bank could come after the property, which affects your investment.

We're planning a virtual meet up in the near future. 

I don't know anything about these specific guys, but my theory for many gurus is that it's easier to find people to buy their course than it is to find and buy really low-priced houses to flip in the right neighborhoods.

If your goal is more FIRE oriented where you 'retire early' - cash flow pretty much has to be a part of that plan the way I see it.For me, cash flow is what justifies the 'daily grind' of being a landlord.  

1) Specifically looking at the midwest, I personally am doing a lot of business in Ohio. 

Specifically, I am interested in multi-family and syndication.

I am not expecting things to work out as you implied but prepare a good exit plan.

@Moira Baggett it's hard to answer without knowing more specifics on what you define as a "failing" syndication investment. 

Does anyone use a tool of some sort to plan out a cash flow tree with rentals? 

I have a few listing agents reject my plan, usually the ones that tell me they have a large database of “buyers” but there are plenty that are hungry and agree.My reasoning is that if they have a large database of “buyers” they will bring those buyers by to see the property.