I likey will just insure the younger boy first. He's more problematic, getting into to things he shouldn't and chewing on varies items. Sometimes I think I have a Puppy that meows. Jackpot was recently into the Veterinarian for a weeping eye and a 3yr. Rabies shot. So he will be the first insured. I'm wondering if Insurance companies charge owners of Purebreds more than others.They can’t insure the cat without knowing if it has pre-existing conditions. You are going to have to provide all your vet records.