I would think this depend on what kinds of tools and how many of each type you have. It is nice to have a few planes on hand to wok with. When one get dull, pick up another. I find it easier (for myself) to sharpen a few irons at a time instead of one at a time. Sometimes I get in a groove and do not want to stop.
I personally like old hand saws for some odd reason. I feel you cannot have too many hand saws. But then again, my wife says I can be a hoarder.
Another thing you might want to think about is, do you have or want children? It might be nice to pass along some tools to them or your grandchildren in the future. When my grandfather passed away I missed out on his tools (did not have a place to store them) and same with my wife grandfather (relatives more worried about getting money. He was a 4th gen german woodworker). I would have loved to had more tools from both. Plus it is a good time to spend with children building things with them.
Of course then there are people like me that are aways up for donations to our tool collections.