I have both Healthy Paws and Trupanion on several dogs. Some puppy buyers have Healthy Paws also. Healthy Paws has been WONDERFUL about everything. No problems in a couple years. One dog had a very expensive dance with Lyme and they covered it cheerfully, no weaseling out of anything. Very fair- no secret loopholes that they find once you've already given the vet the go-ahead, thinking they'll pay it.
Deductible is per year, just like human insurance. I have high coverage/low deductible. Premiums haven't increased much. They've cut me some sizeable checks....$3700 for my poisoned Chihuahua...got the money within days and phone call to see how he was doing.