@JonesFamilyUnits 

"My issue is the payment transaction never deducts from my Tenant Insurance Holding Account so it has a full running balance of insurance collections that never balance to $0.00."

The bill you enter or check you cut to the insurance provider should be assigned the 'Tenant Insurance Holding Account'.  That will reduce the balance in the holding account when you either enter the bill or write the check (depending on how you pay them).