Having had to go through this process when my Mom passed away, I learned that nothing you acquire in "this life" is really important. No matter how much value YOU put on it...there is no guarantee that it won't be thrown away or laid out to be sold to the highest bidder when you are gone.
I do feel kinda weird going into homes for estate sales, some of the same emotions that you experience. I think in the long run though that people would rather someone who appreciates and values those belongings end up with them than trashing them. I do agree that the personal items should be removed though!