Sentimental value:
Some people have a legitimate reason for wanting to let go of something that their loved one had and they passed away. From my experience this past year with my grandpa's death watching my family deal with it made more empathetic in noticing others emotions and how it affects them. It's important in this type of situation to not push them.... If they come to you and say to you they want to deal with it than you can do so but don't push them past where they feel comfortable... Be patient and acknowledge their feelings in the process.
Comfort:
There are times when people like to hold onto items just for the simple fact that we like having them close to you even when others don't really understand why it's so comforting to you. It doesn't matter how long or short you had it. It doesn't even have to be physical, it can be anything that serves as comfort to you. It's hard letting go of something or someone that once was a comforting factor in your life but it's a good thing to be able to show yourself and others that you are strong enough to let go.
The other possibilities are pretty self explanatory...
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