I believe that we are coming to a point in time where you truly have to decide what is more valuable, the items themselves or the sentimentality of the object. At this point the idea of an heirloom is such a retro way of thinking. Few people see these items beyond their collectibility, and I think once you even attempt to apply a value to them, it's time to look at getting rid of them.
I personally like the idea of smaller pieces being passed down, it keeps the intimacy, and it eases the burden on future generations; a burden it looks like you experienced.