We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher by pretending to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

Agree with @Jeff Pollack on having the guts to leave the security of a JOB.

Pros include securing the desired property and strategic planning, while cons involve higher costs, financing challenges, and complexity.

Can you throw out names for Missouri resources they have worked with before on investor friendly realtors, tax experts, and investor friendly banks? 

Depending on the application, first, last, security, and another month or two.

One other market-wide factor I’d throw in is local government policies.

Quote from @Lionel Quiambao:  ... and maybe throw in the option for the tenant for more speed at an increased rent to cover the additional payment. 

Quote from @Jeff Adolphe: @Kevin Collins How long does it typically take you to secure a house with REI?

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.

You have engaged and paid securities attorney and are compliant with Reg D offering