I had our old Samoyed dog insured with Trupanion and was very happy I did. Wish I could have afforded it for all my pets. Maybe one time in six they mistake something for a new illness and apply the deductable again but this has always been easily sorted out. Sometimes the connection between illnesses isn't obvious - especially as different vets and hospitals will explain the same problem in different ways ('cervical neuopathy' is the cause of 'walking difficulty' etc., not two different things.)
They paid thousands without blinking. Must be at least $10k. Well worth it. MRIs, stem cells, gastric torsion surgery. He had better healthcare than I did.
We are currently stuck with Figo for six pets. No claim they can't turn into a complete nightmare disaster. With Trupanion you get a diagnosis and your worries are over. With Figo your pet gets sick and your troubles are just beginning.