What I notice for myself is that over time I come to terms with letting some things go and keeping others.

Part of the equation for me is "what to keep because it will mean something to my son or nieces and nephews down the road? To what extent will they share the since of connectedness through heritage that I have?

Right now, not much. That may well change as they grow older, but the reality is I had my son late in life. He never knew my grandparents, and grew up three states away from extended family and does not have the strong memories and associations of extended family that experience brings. Much of what I value so much because of the emotional memories will be meaningless to my son, and no longer good except for it's monetary value in terms of my meager estate.