I went through some of this last year when my dad died. Sometimes, the worst feelings come from throwing something away. If Mom (or Dad) had use for a particular item, it would feel like a repudiation of them to make it value-less in a dumpster. So if it doesn't get snapped up on eBay or craigslist, consider taking it down to the local goodwill or salvation army.
Someone will find value in it. Make the question for yourself: is this something I value, or would someone else value it more? Then emotionally you've done the right thing. And you can imagine Mom's collection of Cincinnati Enquirer stuff populating the bedrooms of college students everywhere. Your childhood corelle dinnerware being used to serve some other kid's after school snack.
It's still not easy, though!
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per·son \ˈpər-sən\ (noun) - an ephemeral collection of small, irrational decisions
The fun thing about evolution (and science in general) is that it happens whether you believe in it or not.
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