So, communication and assignment issues, as well as not being able to explain the maintenance issues and the required work.3) Proper documentation and quality of work issues.

Or you can sell it, split the equity, and go separate ways.I'm not a fan of borrowing from family/friends unless all parties are honest and everything is documented in a written contract.

Any suggestions I appreciate in advance.Worst case, I'll just create something for him and walk him through things as he goes, but I'm thinking, why not document it for us both (no plans to publish or anything though)!

Refer to the frequently asked questions on the third slide. https://www.hud.gov/sites/dfiles/SFH/documents/MO_203k_Progr...

These lenders often have more flexibility with underwriting and may not require traditional income documentation.

The tenants enjoy using the interface, it is simple to communicate with them as a whole or individually, collect rent payments and see when they are in transit, offer CC payment options at tenants expense, track maintenance request, share documents, and lease the property.Short comings are their financial portion.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

Document the details of this deal as your sample deal.2.

Sometimes you get lucky.You could even bring up the subject of seller financing (search online for ideas of how to structure a seller financed offer), and make sure a competent real estate attorney helps write the offer documents (if it gets that far). 

Instructing or deliberately causing a borrower to sign business-purpose loan documents when you know the money will be used for consumer purposes has always carried civil liabilities.