We have Trupanion for both of our dogs and are pretty happy with them. We almost ended up going with Healthy Paws for Bash, but after really looking through the policies, we decided to stick with Trupanion. Trupanion covers supplements prescribed by your vet, which Healthy paws does not. It may seem like a small thing, but Roxy has been on Welactin and Dasuquin for a while now, and that stuff gets expensive. Also, I liked having the option of choosing to have no deductible. We have made so many claims with them, and we always get a check really fast. Their customer service has been great in the past, too. I will say that our rate increase for Roxy this year was pretty insane. We still come out ahead, though, because Roxy is on a lot of medications for pain/cancer. Her meds and supplements alone would cost us about $300/month without insurance, so paying $90/month for Trupanion, then roughly $30 for the meds still saves us money.
Bash's rate went up $2 per month this year. We'll see what happens as he gets older.
One more thing to mention... Healthy paws covers acupuncture, chiropractic care, etc, whereas Trupanion only covers it if you add on an additional rider (for more money, of course). And, you have to have the rider before anything happens, or it's considered pre-existing. They didn't offer the rider yet when we signed Roxy up, and by the time they did offer it, she was already receiving chiropractic care and acupuncture. Now we can't use the rider, because her condition is pre-existing, even though they didn't offer the coverage before. So we have to pay for acupuncture out of pocket. It's not ideal, but what can we do?
Train the dog in front of you.