The only issue would be how strong your case is to do a 1031 since a family member is living there. 

My issue is finding a property that cashflows with both units rented out.

We have been very fortunate in our RE careers to not have any serious issues with tenants at our properties.

And we like the idea that maintenance shouldn’t be too much of an issue for the first couple of years. 

My layman's thinking is you have not been served as a creditor, and have not been legally barred from reaching out to the tenant, so you can probably simply mail their statement to them and it won't be an issue.

If you set it up with a car rental service like Turo are likely protecting yourself/car more from potential issues and damage and may be able to keep it off platform and only make it available to your renters (not sure on that last part but just a thought).Also, from a lender perspective it could complicate things if you are looking to refinance one day and have car payments included in the lease payments/on the lease.

The former borrower tried to do the right thing to resolve past financial issues. 

They are getting what they really want, and you are crafting the deal to where it will still make sense for you.One potential issue is if what is most important to them is most important to you as well.

My issue was with his intent-it seems he really was only interested in being the buyers broker here as well..  

The issue is that I'm giving up 1/3 equity to a partner and would like to only have me and my father own the final farm.