I'm a very analytical person who won't start a new venture without first gaining a solid understanding, establishing the right framework and connections, and ensuring that I'm securing a great deal.

We started looking at coaching programs and some of these things just seem ridiculous at 20-40 grand, and some seem more like life coaching programs as opposed to real estate programs. we don't want to syndicate we really would just like to find someone that we can bounce deals / ideas off of and have them assist in underwriting and giving us a better sense of security that we are doing the right thing.

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

It's not like we're bundling sub2 deals into tranches and selling them as mortgage-backed securities like they were with subprime mortgages, yet. 

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

This approach ensures you’re making decisions based on logic, not emotion.

Quote from @Stetson Oates: The vast majority of disputes are over security deposits and the most a landlord could lose is 3x the deposit amount.Slip-and-fall or other major lawsuits almost never happen.

That's more like a typical security deposit to rent an apartment, lol. 

From a credit perspective, house hacking also helps you build strong cash flow, which can make it easier to secure financing for future deals.Additionally, if you're targeting high-appreciation markets, you could also look into cash-out refinancing down the line to pull equity and fund additional investments.

I dont allow tenants to move in without first month rent and security deposit paid by cashier check .