I was wondering. Is it worth keeping the protection plan after the free trial 

This is what we are thinking of doing is dropping it after the 6 months and if we need it then add it onI'm going on if Dish still does it like they have in the past, no. When/if you need repair etc get it then there is (or at least has not been) any kind of waiting period. Keep it for the required amount of time then drop it again.