Closet contents...in the box? Or in the heart?

Changing a residence... in my life I have moved across town and across the country...some people do it with far more frequency than I have become accustomed to...after seven moves in four years it has now been TWENTY SIX! years since I hauled out boxes and had to judge all my "stuff" with discerning eyes and decide which will become part of the next move and which will find homes somewhere else...some ..even (gasp) in the trash! Closets and drawers, long just kept shut as museums to no longer needed stuff must now be visited and sorted.
In the attempt to become one of those people who move on, it seems, almost effortlessly and seamlessly from adventure to adventure and place to place because they realize that "stuff" is just..."stuff" I check, sort and toss with determination and my own brand of common sense.
Will the decision making about what to keep or toss get easier as I get older because the weight of some of that past baggage is no longer relevant, or just a little too painful to be carried to the next destination? Is it because I want to keep all the joyful times in my heart instead of in a closet? Do the happy times sing louder if they are not taped up in a box, but instead let free to go round and round in my head?
I feel blessed to be able to agonize over these decisions. The populations of Haiti and Chile, the victims of floods and fires, the homeless and the about to be evicted have those decisions yanked from their power and decided for them in minutes.
How grateful they would be, and I am to be able to grab another box and fill it...now.