Yeah the JWs view cheapens life and leaves uncertainty. One never knows if they had done enough work for the Gov Body to be approved to make it into the kingdom.
I think that's the thing that made death difficult for me as a JW. You never really knew if they were going to be resurrected or not. Sure you put on the happy face & say that you'll see them in the new order but there is always that little doubt in the back of your head. I also felt like I couldn't grieve. I had a friend die when I was about 11. I was crying really hard at the funeral and an elder said something about it to my mother. My mother then told me that I was making a spectacle of myself.
I find death much easier to deal with now as a Christian. When my grandmother (a lifelong Baptist) died, I took a lot of comfort in knowing that she was with the Lord. My church also had grief counselling & support groups which helped me a lot. The people there actually seemed to be concerned with how I was feeling & grieving. Witnesses tend to just read you a scripture & tell you about the hope for the resurrection. You get that feeling that JWs think that by grieving you are showing a lack of faith or something.