The company should absolutely pay for insurance. It's the least they can do for the wrestlers, some of whom get injured again and again, and the WWE's gruelling work schedule is largely responsible for that I feel. If they want them to perform so much, bearing in mind they make a load of money every time that they do, then they should supply insurance.
I also think there should be a wrestler's union within the company, but JR has claimed several times it would never work, and I guess he knows more about it than I do.
Neither idea would make it past Vince Mcmahon anyway. He is as republican as they come.