You should get more nights in the smaller property that can still easily accommodate a family traveling, but is still inexpensive enough to make sense to solo travelers.Cleaning fee impact: Don't you collect this back from your guests?

Are they still collecting rent and taking money that way, or are they billing you? 

All but one of the family members are on board, and we collectively own the majority, but it's 55% and the bank requires 60%.

@Ashley Kehr I use a combination of Apartments.com for rent collection, RentSpree for tenant and background screening, and Stessa for accounting.

A chat bot to tie them up?

How do I go about finding those who'd rather just collect the insurance money then sell it off at a discount?  

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.

Sellers may struggle to mentally shift from "owner" to "tenant," which can create challenges with boundaries and property care.Security Deposit:If you’re doing a temporary leaseback, be sure to collect a substantial security deposit to cover potential damages and ensure they vacate on time.

It offers a lot more than just rent collection.

Rent I could probably collect $2000 a month.